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120205-50-7

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  • (2R,3R)-3-[(S)-1-(tert-Butoxycarbonyl)-pyrrolidin-2-yl]-3-methoxy-2-methylpropanoic acid

    Cas No: 120205-50-7

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120205-50-7 Usage

Uses

(2R,3R)-BOC-dolaproine is an β-methoxy-γ-amino acid component of dolastatin 10, an antineoplastic agent.

Check Digit Verification of cas no

The CAS Registry Mumber 120205-50-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,0,2,0 and 5 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 120205-50:
(8*1)+(7*2)+(6*0)+(5*2)+(4*0)+(3*5)+(2*5)+(1*0)=57
57 % 10 = 7
So 120205-50-7 is a valid CAS Registry Number.

120205-50-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R,3R)-3-((S)-1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid

1.2 Other means of identification

Product number -
Other names (2R,3R)-3-methoxy-2-methyl-3-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]propanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:120205-50-7 SDS

120205-50-7Synthetic route

(S)-t-butyl 2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-((R)-2-oxo-4-phenyloxazolidin-3-yl)propyl)pyrrolidine-1-carboxylate

(S)-t-butyl 2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-((R)-2-oxo-4-phenyloxazolidin-3-yl)propyl)pyrrolidine-1-carboxylate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Stage #1: (S)-t-butyl 2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-((R)-2-oxo-4-phenyloxazolidin-3-yl)propyl)pyrrolidine-1-carboxylate With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran at 0℃; for 3h;
Stage #2: With sodium sulfite In tetrahydrofuran at 20 - 25℃; for 16h;
99%
(4R,5S,2'R,3'R,2
180715-99-5

(4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Stage #1: (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone With dihydrogen peroxide In tetrahydrofuran; water at 0℃; for 0.0833333h;
Stage #2: With water; lithium hydroxide In tetrahydrofuran at 0℃; for 3h;
98%
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h;98%
Stage #1: (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone With dihydrogen peroxide In tetrahydrofuran; water at 0℃; for 0.0833333h;
Stage #2: With lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h;
98%
<2S-<2R*<(R*),α(S*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester
133164-07-5

<2S-<2R*<(R*),α(S*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol for 12h; Ambient temperature;94%
ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate
135383-59-4

ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
With lithium hydroxide In ethanol91%
With lithium hydroxide In ethanol; water at 20℃;59%
With lithium hydroxide In ethanol at 20℃;59%
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
133565-38-5

(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid

methyl iodide
74-88-4

methyl iodide

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Stage #1: (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 0℃;
91%
With sodium hydride In tetrahydrofuran at 0℃; for 18h;89%
Stage #1: (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid; methyl iodide With sodium hydride In tetrahydrofuran at -5 - 0℃; for 75h;
Stage #2: With potassium hydrogensulfate In water pH=2;
72%
C24H34N2O6

C24H34N2O6

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Stage #1: C24H34N2O6 With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran for 4h;
Stage #2: With sodium thiosulfate In tetrahydrofuran
91%
tert-butyl (2S)-2-((1R,2R)-1,3-dimethoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
179039-97-5

tert-butyl (2S)-2-((1R,2R)-1,3-dimethoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 16h;86%
(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine
159173-43-0

(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; water; acetonitrile for 48h;81%
With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; acetonitrile at 20℃; for 72h;75%
Multi-step reaction with 2 steps
1: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h
2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h
View Scheme
Stage #1: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; tert-butyl alcohol for 12h;
Stage #2: With sodium periodate; sodium permanganate In water; acetonitrile at 0 - 5℃; for 4h;
Multi-step reaction with 2 steps
1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 6 h / 20 °C
2: sodium periodate; potassium permanganate / water / 6 h / 0 °C
View Scheme
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
133565-38-5

(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid

A

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

B

(R)-2-((1R,7aS)-3-Oxo-tetrahydro-pyrrolo[1,2-c]oxazol-1-yl)-propionic acid

(R)-2-((1R,7aS)-3-Oxo-tetrahydro-pyrrolo[1,2-c]oxazol-1-yl)-propionic acid

C

[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine
179040-16-5

[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine

Conditions
ConditionsYield
With sodium hydride; methyl iodide In tetrahydrofuran at 0℃; for 48h;A 76%
B 5.3%
C 5.6%
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
133565-38-5

(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid

methyl iodide
74-88-4

methyl iodide

A

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

B

(R)-2-((1R,7aS)-3-Oxo-tetrahydro-pyrrolo[1,2-c]oxazol-1-yl)-propionic acid

(R)-2-((1R,7aS)-3-Oxo-tetrahydro-pyrrolo[1,2-c]oxazol-1-yl)-propionic acid

C

[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine
179040-16-5

[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃; for 48h;A 76%
B 5.3%
C 5.6%
(S)-2-[(1R,2R)-1-Methoxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
120294-47-5

(S)-2-[(1R,2R)-1-Methoxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
(S)-2-((1R,2R)-1-Methoxy-2-methyl-3-oxo-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-2-((1R,2R)-1-Methoxy-2-methyl-3-oxo-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
With potassium permanganate In tert-butyl alcohol for 0.25h; Yield given;
With sodium chlorite; sodium dihydrogenphosphate dihydrate In tert-butyl alcohol at 20℃; for 8h;472 mg
benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate
149606-97-3

benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In water; tert-butyl alcohol
ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate
135383-58-3

ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 45 percent / LHMDS; HMPA / tetrahydrofuran / 0.25 h / -20 °C
2: 59 percent / LiOH*H2O / ethanol; H2O / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1) LHMDS / 1) THF, HMPA
2: 91 percent / aq.LiOH / ethanol
View Scheme
Boc-L-Pro-H
69610-41-9

Boc-L-Pro-H

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: DABCO / CH2Cl2 / 120 h / 20 °C / ultrasound
2: H2 / Pd/C / ethyl acetate / 20 °C
3: 70 percent / proton sponge / CH2Cl2 / 18 h / 20 °C
4: 86 percent / LiOH / tetrahydrofuran; H2O / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 70 percent / Co[P(Ph)3]4 / tetrahydrofuran / 2 h / 0 °C
2.1: 86 percent / 4 Angstroem molecular sieves; proton sponge / CH2Cl2 / 48 h / 20 °C
3.1: aq. H2O2; LiOH*H2O / tetrahydrofuran / 3 h / 0 °C
3.2: 94 percent / sodium sulfite / tetrahydrofuran / 18 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 1.) Et3N, (Bu)2BOTf, 2.) phosphate buffer, 30percent aq. H2O2
2: 1.) aq. H2O2, LiOH, 2.) aq. Na2SO3 / 1.) THF, 3 deg C, 5 h, 2.) THF, 25 deg C, 16 h
3: 76 percent / NaH, MeI / tetrahydrofuran / 48 h / 0 °C
View Scheme
(S)-2-((1R,2R)-1-Hydroxy-2-methoxycarbonyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
164456-57-9

(S)-2-((1R,2R)-1-Hydroxy-2-methoxycarbonyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / proton sponge / CH2Cl2 / 18 h / 20 °C
2: 86 percent / LiOH / tetrahydrofuran; H2O / 16 h / 20 °C
View Scheme
tert-butyl 2-(2-(methoxycarbonyl)-1-hydroxyallyl)pyrrolidine-1-carboxylate
602325-71-3

tert-butyl 2-(2-(methoxycarbonyl)-1-hydroxyallyl)pyrrolidine-1-carboxylate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2 / Pd/C / ethyl acetate / 20 °C
2: 70 percent / proton sponge / CH2Cl2 / 18 h / 20 °C
3: 86 percent / LiOH / tetrahydrofuran; H2O / 16 h / 20 °C
View Scheme
(4R,5S,2'R,3'R,2
133645-51-9

(4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3"-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 86 percent / 4 Angstroem molecular sieves; proton sponge / CH2Cl2 / 48 h / 20 °C
2.1: aq. H2O2; LiOH*H2O / tetrahydrofuran / 3 h / 0 °C
2.2: 94 percent / sodium sulfite / tetrahydrofuran / 18 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) aq. H2O2, LiOH, 2.) aq. Na2SO3 / 1.) THF, 3 deg C, 5 h, 2.) THF, 25 deg C, 16 h
2: 76 percent / NaH, MeI / tetrahydrofuran / 48 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 83 percent / molecular sieves 4A, proton sponge / CH2Cl2 / 48 h / 0 - 20 °C
2: 1.) aq. H2O2, LiOH, 2.) aq. Na2SO3 / 1.) THF, 0 deg C, 3 h, 2.) THF, RT, 12 h
View Scheme
benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate
163768-51-2

benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41 percent / BF3*OEt2 / CH2Cl2
2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / NaH / dimethylformamide / 0.5 h / 0 °C
2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O
View Scheme
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h
2: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
3: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
4: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C
5: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
6: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h
2: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
3: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
4: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature
5: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
6: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 82 percent / BOP, DIEA / CH2Cl2
2: 89 percent / AlLiH4 / tetrahydrofuran / 1 h / Ambient temperature
3: 72 percent / tetrahydrofuran / 3 h / Ambient temperature
4: 90 percent / NaH / dimethylformamide / 24 h / Ambient temperature
5: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h
6: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C
2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h
3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
5: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C
6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 7 steps
1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C
2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h
3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
5: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature
6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
N-(tert-butoxycarbonyl)-L-prolinol
69610-40-8

N-(tert-butoxycarbonyl)-L-prolinol

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
2: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
3: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C
4: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
5: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
2: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
3: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature
4: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
5: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine; dimethyl sulfoxide / 0.25 h / 5 - 10 °C
1.2: 2 h / 0 °C
2.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.75 h / 0 °C
2.2: 3 h / -78 - 25 °C
2.3: 1 h / 0 °C
3.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 48 h / 0 - 25 °C / Molecular sieve
4.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran / 3 h / 0 °C
4.2: 16 h / 20 - 25 °C
View Scheme
<2S-<2R*<(R*),α(R*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-hydroxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester
133120-83-9

<2S-<2R*<(R*),α(R*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-hydroxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C
2: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
3: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature
2: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
3: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
<2S-<2R*<(R*),α(R*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester
133120-84-0

<2S-<2R*<(R*),α(R*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
2: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
L-proline
147-85-3

L-proline

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C
2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h
3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
5: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C
6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 7 steps
1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C
2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h
3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h
5: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature
6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C
7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature
View Scheme
tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate
115186-37-3

tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 89 percent / AlLiH4 / tetrahydrofuran / 1 h / Ambient temperature
2: 72 percent / tetrahydrofuran / 3 h / Ambient temperature
3: 90 percent / NaH / dimethylformamide / 24 h / Ambient temperature
4: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h
5: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h
View Scheme
(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine
159173-40-7

(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / NaH / dimethylformamide / 24 h / Ambient temperature
2: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h
3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / mineral oil; hexane; N,N-dimethyl-formamide / 2 h / 0 - 5 °C
2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 12 h
2.2: 4 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.67 h / 0 - 20 °C / Inert atmosphere
2: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 6 h / 20 °C
3: sodium periodate; potassium permanganate / water / 6 h / 0 °C
View Scheme
(S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
120205-60-9

(S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: BF3*Et2O
2: 57 percent / potassium tert-butoxide / tetrahydrofuran / -20 °C
3: H2 / Pd/C
View Scheme
(S)-2-[(1R,2S)-1-Methoxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
120205-61-0, 120294-47-5

(S)-2-[(1R,2S)-1-Methoxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 57 percent / potassium tert-butoxide / tetrahydrofuran / -20 °C
2: H2 / Pd/C
View Scheme
(S)-tert-butyl 2-((R)-3-ethoxy-1-hydroxy-3-oxopropyl)pyrrolidine-1-carboxylate
108142-95-6

(S)-tert-butyl 2-((R)-3-ethoxy-1-hydroxy-3-oxopropyl)pyrrolidine-1-carboxylate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1) LDA / 1) THF, HMPA, -78 deg C, 2) -78 deg C to -20 deg C, 2.5 h
2: 1) LDA, 2) MeOH / 1) THF, -20 deg C, 1 h, 2) -78 deg C
3: 1) LHMDS / 1) THF, HMPA
4: 91 percent / aq.LiOH / ethanol
View Scheme
(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine
130199-65-4

(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate
120205-54-1

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 75h;100%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide 1) 0 deg C, 2 h, 2) RT;98%
With triethylamine; diethyl dicarbonate In N,N-dimethyl-formamide97.5%
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;81%
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;81%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

tert-butyl (2S)-2-((1R,2R)-1,3-dimethoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
179039-97-5

tert-butyl (2S)-2-((1R,2R)-1,3-dimethoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
In methanol; diethyl ether; hexane at 0 - 20℃; for 0.166667h;100%
methanol
67-56-1

methanol

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoic acid methyl ester
179040-04-1

(2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃;100%
With thionyl chloride at 0 - 20℃;44 mg
ethanol
64-17-5

ethanol

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

ethyl (2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoate hydrochloride

ethyl (2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 18h;100%
With thionyl chloride at 0 - 20℃; for 18h;100%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoic acid methyl ester
179040-04-1

(2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride In methanol at 20℃;100%
(1S,2R)-(+)-norphedrine
37577-28-9

(1S,2R)-(+)-norphedrine

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

tert-butyl (2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate
160800-65-7

tert-butyl (2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;98%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;98%
With diethyl cyanophosphonate; triethylamine at 0 - 20℃; for 6h; Inert atmosphere;98%
(S)-methyl 4-amino-2-methyl-5-phenylpent-2-enoate

(S)-methyl 4-amino-2-methyl-5-phenylpent-2-enoate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

C27H40N2O6

C27H40N2O6

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;98%
(1S,2R)-(+)-norphedrine
37577-28-9

(1S,2R)-(+)-norphedrine

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

tert-butyl (S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

tert-butyl (S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;98%
C12H15NO2

C12H15NO2

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

C26H38N2O6

C26H38N2O6

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;95%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-3-methoxy-5-methyl-1-oxo-1-(pentafluorophenoxy)heptan-4-yl]-N-methyl-L-valinamide

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-3-methoxy-5-methyl-1-oxo-1-(pentafluorophenoxy)heptan-4-yl]-N-methyl-L-valinamide

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-2-carboxy-1-methoxypropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-2-carboxy-1-methoxypropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Conditions
ConditionsYield
Stage #1: N-Boc-(2R,3R,4S)-dolaproine With hydrogenchloride at 20℃; for 6h;
Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-3-methoxy-5-methyl-1-oxo-1-(pentafluorophenoxy)heptan-4-yl]-N-methyl-L-valinamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;
92%
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
161485-82-1

(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 5.5h; Inert atmosphere;90%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;83%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;83%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(S)-2-(benzyloxy)-1-hydroxy-3-phenylpropane
123394-79-6

(S)-2-(benzyloxy)-1-hydroxy-3-phenylpropane

(S)-2-[(1R,2R)-2-((S)-2-Benzyloxy-3-phenyl-propoxycarbonyl)-1-methoxy-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-2-[(1R,2R)-2-((S)-2-Benzyloxy-3-phenyl-propoxycarbonyl)-1-methoxy-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 12h;86%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-phenyl-propan-2-ol
173180-05-7

(S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-phenyl-propan-2-ol

(S)-2-{(1R,2R)-2-[(S)-1-Benzyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxycarbonyl]-1-methoxy-propyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
173180-10-4

(S)-2-{(1R,2R)-2-[(S)-1-Benzyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxycarbonyl]-1-methoxy-propyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 11h;85%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
161485-82-1

(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;85%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;85%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;85%
(4R)-methyl-4-amino-2-methyl-5-phenylpentanoate

(4R)-methyl-4-amino-2-methyl-5-phenylpentanoate

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

C27H42N2O6

C27H42N2O6

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;84%
5-(1'-ethyl-2'-amino)isoquinoline

5-(1'-ethyl-2'-amino)isoquinoline

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

5-(1'-ethyl-2'-amido-Boc-Dap)isoquinoline

5-(1'-ethyl-2'-amido-Boc-Dap)isoquinoline

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;84%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(S)-tert-butyl 2-amino-3-(2-fluorophenyl)propanoate

(S)-tert-butyl 2-amino-3-(2-fluorophenyl)propanoate

(S)-tert-butyl 2-((1R,2R)-3-(((S)-1-(tert-butoxy)-3-(2-fluorophenyl)-1-oxopropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

(S)-tert-butyl 2-((1R,2R)-3-(((S)-1-(tert-butoxy)-3-(2-fluorophenyl)-1-oxopropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20 - 30℃; for 2h; Inert atmosphere;83.9%
(S)-methyl 2-amino-3-phenylpropanoate hydrochloride

(S)-methyl 2-amino-3-phenylpropanoate hydrochloride

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
161485-82-1

(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;83%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;83%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(S)-methyl 2-amino-3-(4-fluorophenyl)propanoate hydrochloride

(S)-methyl 2-amino-3-(4-fluorophenyl)propanoate hydrochloride

(S)-tert-butyl 2-((1R,2R)-3-(((S)-3-(4-fluorophenyl)-1-methoxy-1-oxopropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

(S)-tert-butyl 2-((1R,2R)-3-(((S)-3-(4-fluorophenyl)-1-methoxy-1-oxopropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile at 23℃; for 12h; Inert atmosphere;82.6%
tyrosamine
51-67-2

tyrosamine

N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

N-Boc-Dap-4-hydroxyphenethylamide
1307229-20-4

N-Boc-Dap-4-hydroxyphenethylamide

Conditions
ConditionsYield
Stage #1: N-Boc-(2R,3R,4S)-dolaproine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: tyrosamine In N,N-dimethyl-formamide at 20℃; for 16h;
82%
Stage #1: N-Boc-(2R,3R,4S)-dolaproine With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: tyrosamine In N,N-dimethyl-formamide at 20℃; for 16h;
82%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethanamine, hydrochloride salt
135383-60-7

(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethanamine, hydrochloride salt

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate
120205-54-1

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 20h;81%
With triethylamine; diethyl dicarbonate In 1,2-dimethoxyethane at 4℃; for 14h;78%
N-Boc-(2R,3R,4S)-dolaproine
120205-50-7

N-Boc-(2R,3R,4S)-dolaproine

(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine trifluoroacetic acid salt

(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine trifluoroacetic acid salt

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate
120205-54-1

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;81%
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;81%
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;81%

120205-50-7Relevant articles and documents

Synthesis of both syn and anti diastereoisomers of Boc-dolaproine from (S)-proline through DKR using ruthenium-catalyzed hydrogenation: A dramatic role of N-protecting groups

Mordant, Céline,Reymond, Sébastien,Ratovelomanana-Vidal, Virginie,Genêt, Jean-Pierre

, p. 9715 - 9723 (2004)

The natural (2R,3R)-Boc-dolaproine and its unnatural (2S,3S) diastereoisomer were synthesized involving as key transformation the Ru(II)-promoted hydrogenation of the β-keto-α-methyl ester derived from (S)-N-Boc-proline. Interestingly, the asymmetric hydrogenation of this β-keto ester N-protected as an amine hydrochloride salt, provided the corresponding anti (2S,3R)- and (2R,3S)-β-hydroxy-α-methyl esters with significant level of selectivities through dynamic kinetic resolution. Graphical Abstract.

An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction

Almeida, Wanda P.,Coelho, Fernando

, p. 937 - 940 (2003)

In this communication we report a stereoselective total synthesis of N-Boc-dolaproine (Dap), an amino acid residue of the antineoplastic pentapeptide Dolastatin 10. Our strategy is based on a Baylis-Hillman reaction between N-Boc-prolinal and methyl acrylate, followed by a diastereoselective double bond hydrogenation and hydrolysis of the ester function.

EFFICIENT PREPARATION OF DOLASTATIN AND AURISTATIN ANALOGS THROUGH A COMMON INTERMEDIATE

-

Paragraph 0087, (2021/09/17)

Methods for making a dolastatin, auristatin or related compounds comprising the steps of providing a universal dolastatin core of Formula (I) reacting the C-terminal carboxylic acid group with an amine (A) to form an amide bond and reacting the N-terminal amine with a carboxylic acid (CA) to form an amide bond, wherein the steps can be performed in either order. Also provided are an isolated salt of the universal dolastatin core for use in preparation of dolastatins, auristatins and related compounds. Also provided are a number of intermediates and process steps which are useful for the preparation of high purity dolastatin core and high purity dolastatin and auristatin compounds.

Synthesis method of N-Boc-Dolaproine and synthesis method of Boc-Dap DCHA

-

, (2020/07/21)

The invention discloses a synthesis method of N-Boc-Dolaproine and a synthesis method of Boc-Dap DCHA. The synthesis method comprises the following steps: 1) subjecting a compound shown in the specification and a compound shown in the specification to a Reformatsky reaction under the activation of zinc powder to synthesize a compound shown in the specification, with X being Cl or Br or I, and R being alkane or olefin; 2) subjecting the compound shown in the specification to methylation to obtain a compound shown in the specification; 3) carrying out a hydrolysis reaction on the compound shownin the specification so as to obtain N-Boc-Dolaproine. By applying the technical scheme of the invention, the yield of each step of reaction is relatively good, the intermediates are easy to purify, the process route used by the method is relatively short, the material price is relatively low, the synthesis process is simple to operate, the production cost is further reduced, and the methods can be applied to industrial production.

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