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35661-39-3

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35661-39-3 Usage

Chemical Properties

white to light yellow crystal powde

Uses

N-Fmoc-L-alanine is potentially useful for proteomics studies and solid phase peptide synthesis techniques. Alanine is one of the simplest amino acids - a methyl group as the side chain. This small side chain confers a high degree of flexibility when incorporated into a polypeptide chain. The Fmoc group is typically removed with a base such as pyridine - an orthogonal de-protection strategy to the acid labilie Boc group.

Check Digit Verification of cas no

The CAS Registry Mumber 35661-39-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,6,6 and 1 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 35661-39:
(7*3)+(6*5)+(5*6)+(4*6)+(3*1)+(2*3)+(1*9)=123
123 % 10 = 3
So 35661-39-3 is a valid CAS Registry Number.
InChI:InChI=1/C18H17NO4/c1-11(17(20)21)19-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,19,22)(H,20,21)/p-1/t11-/m0/s1

35661-39-3 Well-known Company Product Price

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  • TCI America

  • (F0305)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-alanine Hydrate  >98.0%(HPLC)(T)

  • 35661-39-3

  • 5g

  • 220.00CNY

  • Detail
  • TCI America

  • (F0305)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-alanine Hydrate  >98.0%(HPLC)(T)

  • 35661-39-3

  • 25g

  • 750.00CNY

  • Detail
  • Alfa Aesar

  • (H59438)  N-Fmoc-L-alanine, 95%   

  • 35661-39-3

  • 5g

  • 174.0CNY

  • Detail
  • Alfa Aesar

  • (H59438)  N-Fmoc-L-alanine, 95%   

  • 35661-39-3

  • 25g

  • 870.0CNY

  • Detail
  • Aldrich

  • (531480)  Fmoc-Ala-OH  95%

  • 35661-39-3

  • 531480-5G

  • 243.36CNY

  • Detail
  • Aldrich

  • (531480)  Fmoc-Ala-OH  95%

  • 35661-39-3

  • 531480-100G

  • 939.51CNY

  • Detail
  • Aldrich

  • (531480)  Fmoc-Ala-OH  95%

  • 35661-39-3

  • 531480-25G

  • 334.62CNY

  • Detail
  • Aldrich

  • (531480)  Fmoc-Ala-OH  95%

  • 35661-39-3

  • 531480-1KG

  • 8,371.35CNY

  • Detail

35661-39-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

1.2 Other means of identification

Product number -
Other names Fmoc-L-alpha-Alanine

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:35661-39-3 SDS

35661-39-3Synthetic route

C32H27NO5

C32H27NO5

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 1h; Irradiation;100%
L-alanin
56-41-7

L-alanin

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 18h;99%
With sodium carbonate In N,N-dimethyl-formamide for 0.166667h; Ambient temperature;96%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 18h;
L-alanin
56-41-7

L-alanin

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;96%
In ethanol; water at 60℃; for 4h; chemoselective reaction;86%
L-alanin
56-41-7

L-alanin

polymer-bound Fmoc-O-succinimide

polymer-bound Fmoc-O-succinimide

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 24h;95%
L-alanin
56-41-7

L-alanin

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-oxo-2-(piperidin-1-yl)acetimidoyl cyanide
1370440-36-0

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-oxo-2-(piperidin-1-yl)acetimidoyl cyanide

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone93.2%
L-alanin
56-41-7

L-alanin

(9-fluorenyl)methyl pentafluorophenyl carbonate
88744-04-1

(9-fluorenyl)methyl pentafluorophenyl carbonate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone Ambient temperature;93%
L-alanin
56-41-7

L-alanin

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-(ethylamino)-2-oxoacetimidoyl cyanide
1370440-32-6

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-(ethylamino)-2-oxoacetimidoyl cyanide

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone92.6%
L-alanin
56-41-7

L-alanin

Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester
99503-04-5

Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With tertiary amine In 1,4-dioxane; water for 3h;91%
L-alanin
56-41-7

L-alanin

Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester

Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 2h;91%
ether-petroleum ether

ether-petroleum ether

L-alanin
56-41-7

L-alanin

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
In 1,4-dioxane; sodium carbonate90.2%
L-alanin
56-41-7

L-alanin

9-fluorenylmethyl N-succinimidyl carbonate
102774-86-7

9-fluorenylmethyl N-succinimidyl carbonate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With triethylamine In water; acetonitrile for 1h;90%
Fmoc-Ala-OTIPS

Fmoc-Ala-OTIPS

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With potassium fluoride In tetrahydrofuran; methanol at 22℃; for 2h;86%
Fmoc-Ala-OSEM

Fmoc-Ala-OSEM

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With magnesium bromide ethyl etherate In dichloromethane at -20 - 22℃; for 3.5h;84%
Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine
135248-89-4

Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; triethyl phosphite In aq. phosphate buffer; acetonitrile at 20℃; for 0.5h; pH=6.5; Irradiation;84%
methyl 2-(((9H-fluoren-9-yl)methoxy)carbonyl)aminopropanoate
146346-88-5

methyl 2-(((9H-fluoren-9-yl)methoxy)carbonyl)aminopropanoate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With trimethyltin hydroxide In 1,2-dichloro-ethane at 80℃; for 5h;75%
(2S)-N-<(fluoren-9-yl)methoxycarbonyl>alanine prop-2-enyl ester
146549-15-7

(2S)-N-<(fluoren-9-yl)methoxycarbonyl>alanine prop-2-enyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With water; chlortris(triphenylphosphine)rhodium In ethanol for 1h;67%
(S)-(4'-((4-((2-(((9H-fluoren-9-yl)methoxy)carbonylamino)propanoyloxy)methyl)phenoxy)methyl)biphenyl-4-yl)triphenylphosphonium perchlorate

(S)-(4'-((4-((2-(((9H-fluoren-9-yl)methoxy)carbonylamino)propanoyloxy)methyl)phenoxy)methyl)biphenyl-4-yl)triphenylphosphonium perchlorate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0℃; for 1.5h;61%
N-Fmoc-L-alanine linked to Wang-resin

N-Fmoc-L-alanine linked to Wang-resin

A

L-alanin
56-41-7

L-alanin

B

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With bis(tri-n-butyltin)oxide In chloroform at 61℃; for 60h;A 40%
B 18%
C21H25NO4Si

C21H25NO4Si

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With methanol In dichloromethane for 0.5h; Ambient temperature; Yield given;
N-(9-fluorenylmethyloxycarbonyl)alanine 3,4,5-tris(octadecyloxy)benzyl ester
233281-32-8

N-(9-fluorenylmethyloxycarbonyl)alanine 3,4,5-tris(octadecyloxy)benzyl ester

A

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

B

5-(bromomethyl)-1,2,3-tris(octadecyloxy)benzene
955095-33-7

5-(bromomethyl)-1,2,3-tris(octadecyloxy)benzene

Conditions
ConditionsYield
With hydrogen bromide In acetic acid
N-(9-fluorenylmethyloxycarbonyl)alanine 3,4,5-tris(octadecyloxy)benzyl ester
233281-32-8

N-(9-fluorenylmethyloxycarbonyl)alanine 3,4,5-tris(octadecyloxy)benzyl ester

A

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

B

(3,4,5-trioctadecyloxyphenyl)methan-1-ol
233281-31-7

(3,4,5-trioctadecyloxyphenyl)methan-1-ol

Conditions
ConditionsYield
With hydrogenchloride In ethyl acetate at 20℃;
N-Fmoc-L-alanine phenacyl ester

N-Fmoc-L-alanine phenacyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With magnesium; acetic acid In methanol; N,N-dimethyl-formamide at 20℃; for 75h;
PEGA1900-resin-NH-(p-COC6H4CH2)-(S)-OCOCH(CH3)NHFmoc

PEGA1900-resin-NH-(p-COC6H4CH2)-(S)-OCOCH(CH3)NHFmoc

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With chymotrypsin In phosphate buffer for 16h; pH=8;
PEGA1900-resin-NH-(p-COCH2OC6H4CH2)-(S)-OCOCH(CH3)NHFmoc

PEGA1900-resin-NH-(p-COCH2OC6H4CH2)-(S)-OCOCH(CH3)NHFmoc

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Conditions
ConditionsYield
With chymotrypsin In phosphate buffer for 16h; pH=8;
Fmoc-Ala-MFE
910126-27-1

Fmoc-Ala-MFE

A

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

B

3-O-methylfluorescein
70672-05-8

3-O-methylfluorescein

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; cathepsin B In phosphate buffer at 37℃; pH=6.7; Enzyme kinetics;
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

N-(9-fluorenylmethoxycarbonyl)-L-alanyl fluoride
142061-92-5, 145434-41-9, 130858-92-3

N-(9-fluorenylmethoxycarbonyl)-L-alanyl fluoride

Conditions
ConditionsYield
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 20℃; for 15h;100%
With trifluoro-[1,3,5]triazine; triethylamine In dichloromethane at -40℃; for 2h;93%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane for 4h; Ambient temperature; or in MeCN;85%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

9H-fluoren-9-ylmethyl [(1S)-2-chloro-1-methyl-oxoethyl]carbamate
103321-50-2

9H-fluoren-9-ylmethyl [(1S)-2-chloro-1-methyl-oxoethyl]carbamate

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 60℃; for 0.5h; Inert atmosphere;100%
With thionyl chloride In dichloromethane for 0.5h; Reflux;98%
With thionyl chloride In dichloromethane at 20℃; for 0.366667h; Sonication;96%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

(S)-2-(N-fluorenylmethoxycarbonylamino)propanol
161529-13-1

(S)-2-(N-fluorenylmethoxycarbonylamino)propanol

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With 4-methyl-morpholine In 1,2-dimethoxyethane at -15℃; for 1h;
Stage #2: With sodium tetrahydroborate In 1,2-dimethoxyethane; water at -15℃; Further stages.;
100%
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With isobutyl chloroformate In 1,2-dimethoxyethane at -15℃; for 0.0166667h; Acylation;
Stage #2: With sodium tetrahydroborate In 1,2-dimethoxyethane at -15℃; for 0.00833333h; Reduction;
91%
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate In water; ethyl acetate at 0℃; for 0.416667h;
88%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

salvinorin B
92545-30-7

salvinorin B

2-O-{(S)-2-[N-(9-fluorenylmethoxycarbonyl)amino]propionyl}salvinorin B

2-O-{(S)-2-[N-(9-fluorenylmethoxycarbonyl)amino]propionyl}salvinorin B

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 22h;100%
With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 50℃; for 24h;
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Ile-Wang resin

Fmoc-Ile-Wang resin

Ala-Ile-Wang resin

Ala-Ile-Wang resin

Conditions
ConditionsYield
Stage #1: Fmoc-Ile-Wang resin With piperidine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h;
Stage #3: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.25h;
100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

N-Fmoc-D-Glu α-amide γ-tert-butyl ester
104090-93-9

N-Fmoc-D-Glu α-amide γ-tert-butyl ester

2-N-acetyl-1-β-O-allyl 4,6-O-isopropylidenemuramic acid
364368-47-8

2-N-acetyl-1-β-O-allyl 4,6-O-isopropylidenemuramic acid

2-N-acetyl-1-β-O-allyl-muramoyl-L-alanyl-D-isoglutamine tert-butyl ester
364368-41-2

2-N-acetyl-1-β-O-allyl-muramoyl-L-alanyl-D-isoglutamine tert-butyl ester

Conditions
ConditionsYield
Multistep reaction.;100%
(3,4-dimethoxy-phenethylamino)acetic acid allyl ester
916598-58-8

(3,4-dimethoxy-phenethylamino)acetic acid allyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

N-[(9H-fluorenyl-9-ylmethoxy)carbonyl]-L-alanyl-N-(3,4-dimethoxyphenethyl)glycine allyl ester
916598-60-2

N-[(9H-fluorenyl-9-ylmethoxy)carbonyl]-L-alanyl-N-(3,4-dimethoxyphenethyl)glycine allyl ester

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With 4-methyl-morpholine; isobutyl chloroformate In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: (3,4-dimethoxy-phenethylamino)acetic acid allyl ester In N,N-dimethyl-formamide at 20℃;
100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

monomethoxy-polyethylene glycol

monomethoxy-polyethylene glycol

N-(9-fluorenylmethoxycarbonyl)-L-alanine terminated monomethoxy-polyethylene glycol

N-(9-fluorenylmethoxycarbonyl)-L-alanine terminated monomethoxy-polyethylene glycol

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

N-(9-fluorenylmethoxycarbonyl)-D-alanine
35661-38-2, 35661-39-3, 79990-15-1

N-(9-fluorenylmethoxycarbonyl)-D-alanine

H-(D)Ala-Ala-(D)-Ala-Lys(Boc)-(D)Ala-Lys(Boc)-OH
959924-65-3

H-(D)Ala-Ala-(D)-Ala-Lys(Boc)-(D)Ala-Lys(Boc)-OH

Conditions
ConditionsYield
Multistep reaction.;100%
6-(tert-butoxycarbonylamino)hexanoic acid
6404-29-1

6-(tert-butoxycarbonylamino)hexanoic acid

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Boc-Ahx-Val-Ala-OH
1000018-75-6

Boc-Ahx-Val-Ala-OH

Conditions
ConditionsYield
Multistep reaction.;100%
C42H37ClNO6Pol

C42H37ClNO6Pol

C29H31NO5

C29H31NO5

N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

O-benzyl-N-Fmoc-L-serine
122889-11-6, 83792-48-7

O-benzyl-N-Fmoc-L-serine

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Ser(tBu)-OH
71989-33-8

Fmoc-Ser(tBu)-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Nα-FMOC-Nω-L-tosylarginine
139090-50-9, 83792-47-6

Nα-FMOC-Nω-L-tosylarginine

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine
146346-82-9

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine

N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester
146982-24-3

N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester

Z-Phe-Ala-Thr(TBS)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(tBu)-Asp(OAll)-Ser(Bzl)-Asp(OtBu)-OH
1240360-55-7

Z-Phe-Ala-Thr(TBS)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(tBu)-Asp(OAll)-Ser(Bzl)-Asp(OtBu)-OH

Conditions
ConditionsYield
Stage #1: C42H37ClNO6Pol With morpholine Automated synthesizer; solid phase reaction;
Stage #2: O-benzyl-N-Fmoc-L-serine With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole In 1-methyl-pyrrolidin-2-one Automated synthesizer; solid phase reaction;
Stage #3: C29H31NO5; N-Cbz-L-Phe; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Nα-FMOC-Nω-L-tosylarginine; N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine; N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester Further stages;
100%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Ile-OH
71989-23-6

Fmoc-Ile-OH

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester
143824-78-6

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester

H2N-Gly-Trp(Boc)-Leu-Ala-Ala-Ile-Leu-Gly-OH
1234926-33-0

H2N-Gly-Trp(Boc)-Leu-Ala-Ala-Ile-Leu-Gly-OH

Conditions
ConditionsYield
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Automated synthesizer; solid phase reaction;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.1h; Automated synthesizer; solid phase reaction;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Ile-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester Further stages;
100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

5-fluoro-N1-(4-fluorophenyl)benzene-1,2-diamine

5-fluoro-N1-(4-fluorophenyl)benzene-1,2-diamine

(S)-(9H-fluoren-9-yl)methyl 1-(4-fluoro-2-(4-fluorophenylamino)phenylamino)-1-oxopropan-2-ylcarbamate
1338481-96-1

(S)-(9H-fluoren-9-yl)methyl 1-(4-fluoro-2-(4-fluorophenylamino)phenylamino)-1-oxopropan-2-ylcarbamate

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -10℃; for 0.5h;
Stage #2: 5-fluoro-N1-(4-fluorophenyl)benzene-1,2-diamine In dichloromethane at -10℃; for 1h;
100%
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -10℃; for 0.5h;
Stage #2: 5-fluoro-N1-(4-fluorophenyl)benzene-1,2-diamine In dichloromethane at -10℃; for 1h;
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine
312746-41-1

N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine

C2HF3O2*C17H24N4O3Se
1607794-60-4

C2HF3O2*C17H24N4O3Se

Conditions
ConditionsYield
Stage #1: Fmoc-Pro-OH With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1.5h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.2h;
Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; trifluoroacetic acid; N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine Further stages;
100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine
312746-41-1

N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine

C2HF3O2*C26H33N5O4Se2
1607794-62-6

C2HF3O2*C26H33N5O4Se2

Conditions
ConditionsYield
Stage #1: N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1.5h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.2h;
Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; trifluoroacetic acid; N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine Further stages;
100%
6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid
159610-89-6

6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid

Fmoc-gly-wang resin

Fmoc-gly-wang resin

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

N-α-Fmoc-N-ε-biotinyl-L-lysine
146987-10-2

N-α-Fmoc-N-ε-biotinyl-L-lysine

C67H113N21O17S

C67H113N21O17S

Conditions
ConditionsYield
Stage #1: Fmoc-gly-wang resin With piperidine In N,N-dimethyl-formamide for 0.333333h; SASRIN®-resin;
Stage #2: Fmoc-Pro-OH With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide pH=8 - 9; SASRIN®-resin;
Stage #3: 6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Lys(tert-butoxycarbonyl); N-α-Fmoc-N-ε-biotinyl-L-lysine Further stages;
100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

1-methyl-1-phenylethyl 2,2,2-trichloroacetimidoate
147221-33-8

1-methyl-1-phenylethyl 2,2,2-trichloroacetimidoate

Fmoc-Ala-OCumyl

Fmoc-Ala-OCumyl

Conditions
ConditionsYield
In dichloromethane at 20℃; for 16h;100%
In dichloromethane at 10℃; for 1h;98%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

HCl*H-Gln(Trt)-Ser(ψMe,M ePro)-Gly-Leu-Gly-Cys(Trt)-Asn(Trt)-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-Okb, Kb=2,4-didocosyloxybenzyl

HCl*H-Gln(Trt)-Ser(ψMe,M ePro)-Gly-Leu-Gly-Cys(Trt)-Asn(Trt)-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-Okb, Kb=2,4-didocosyloxybenzyl

HCl*H-Ala-Gln(Trt)-Ser(ψM e,M ePro)-Gly-Leu-Gly-Cys(Trt)-Asn(Trt)-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-Okb, Kb=2,4-didocosyloxybenzyl

HCl*H-Ala-Gln(Trt)-Ser(ψM e,M ePro)-Gly-Leu-Gly-Cys(Trt)-Asn(Trt)-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-Okb, Kb=2,4-didocosyloxybenzyl

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; HCl*H-Gln(Trt)-Ser(ψMe,M ePro)-Gly-Leu-Gly-Cys(Trt)-Asn(Trt)-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-Okb, Kb=2,4-didocosyloxybenzyl With N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With piperidine; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; N,N-dimethyl-formamide pH=Ca. 6;
100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

(S)-(-)-3-aminopiperidin-2-one
34294-79-6

(S)-(-)-3-aminopiperidin-2-one

(9H-fluoren-9-yl)methyl ((S)-1-oxo-1-(((S)-2-oxopiperidin-3-yl)amino)propan-2-yl)carbamate

(9H-fluoren-9-yl)methyl ((S)-1-oxo-1-(((S)-2-oxopiperidin-3-yl)amino)propan-2-yl)carbamate

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 N,N-dimethyl-formamide Inert atmosphere;100%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

acetic anhydride
108-24-7

acetic anhydride

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

Fmoc-His(Trt)-OH
109425-51-6

Fmoc-His(Trt)-OH

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester
143824-78-6

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

Ac-GGAK(Boc)R(Pbf)H(Trt)R(Pbf)W(Boc)W(Boc)-NH2

Ac-GGAK(Boc)R(Pbf)H(Trt)R(Pbf)W(Boc)W(Boc)-NH2

Conditions
ConditionsYield
Stage #1: 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Enzymatic reaction;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.2h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; acetic anhydride; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-His(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;
100%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

C62H119NO4

C62H119NO4

C80H134N2O7

C80H134N2O7

Conditions
ConditionsYield
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃; for 5h;100%
formaldehyd
50-00-0

formaldehyd

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

9H-fluoren-9-ylmethyl (S)-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate
83999-95-5

9H-fluoren-9-ylmethyl (S)-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 2h; Reagent/catalyst; Temperature; Reflux;99%
With toluene-4-sulfonic acid In acetonitrile at 120℃; for 0.0333333h; microwave irradiation;97%
With toluene-4-sulfonic acid In toluene for 0.5h; Heating;96%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

2,4-dichlorophenyl-4-bromomethyl-phenoxyacetate
126771-40-2

2,4-dichlorophenyl-4-bromomethyl-phenoxyacetate

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propionic acid 4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl ester
126771-54-8

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propionic acid 4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3h; Ambient temperature;99%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Met-Ala-Ile-Pro-t-Bu

Met-Ala-Ile-Pro-t-Bu

N-Fmoc-L-Ala-L-Met-L-Ala-L-Ile-L-Pro-t-Bu

N-Fmoc-L-Ala-L-Met-L-Ala-L-Ile-L-Pro-t-Bu

Conditions
ConditionsYield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Addition; Peptide-bond formation;99%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

(S)-2-[(4-Chloro-benzyl)-(2-nitro-benzenesulfonyl)-amino]-propionic acid

(S)-2-[(4-Chloro-benzyl)-(2-nitro-benzenesulfonyl)-amino]-propionic acid

Conditions
ConditionsYield
Multistep reaction;99%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

(2S)-N-allyloxycarbonyl-L-proline
110637-44-0

(2S)-N-allyloxycarbonyl-L-proline

Pro-Pro-Ala-Fmoc

Pro-Pro-Ala-Fmoc

Conditions
ConditionsYield
Multistep reaction;99%
(4R,2'S)-2-[1'-Alloc-Thr(propargyl)-pyrrolidin-2'-yl]-4-(3
863671-84-5

(4R,2'S)-2-[1'-Alloc-Thr(propargyl)-pyrrolidin-2'-yl]-4-(3"-chloro-benzyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

(4R,2'S)-2-[1'-Fmoc-Ala-Thr(propargyl)-pyrrolidin-2'-yl]-4-(3-chloro-benzyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
863671-85-6

(4R,2'S)-2-[1'-Fmoc-Ala-Thr(propargyl)-pyrrolidin-2'-yl]-4-(3-chloro-benzyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: (4R,2'S)-2-[1'-Alloc-Thr(propargyl)-pyrrolidin-2'-yl]-4-(3"-chloro-benzyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 2h;
Stage #2: (4R,2'S)-2-[1'-Alloc-Thr(propargyl)-pyrrolidin-2'-yl]-4-(3"-chloro-benzyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester With 1,4-diaza-bicyclo[2.2.2]octane; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 20℃; for 0.333333h;
99%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

3β-hydroxy-pregn-4-en-20-one
566-66-5

3β-hydroxy-pregn-4-en-20-one

C39H47NO5
1185296-15-4

C39H47NO5

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;99%

35661-39-3Relevant articles and documents

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.

supporting information, p. 8297 - 8302 (2021/03/01)

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases

Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae

, p. 332 - 338 (2019/04/13)

Liquid chromatographic enantiomer separation and simultaneous determination of chemical and enantiomeric purity of α-amino acids and their methyl esters as N-fluorenylmethoxycarbonyl (FMOC) derivatives was performed on three covalently bonded type chiral stationary phases (CSPs) derived from amylose derivatives. The enantiomer separation of α-amino acid esters as N-FMOC derivatives was better than that of the corresponding acids, especially for CSP 1 and 2. Chemical impurities as the corresponding racemic acids present in several commercially available racemic amino acid methyl esters were observed to be 0.49–17.50%. Enantiomeric impurities of several commercially available L-amino acid methyl esters were found to be 0.03–0.58%, whereas chemical impurities as the corresponding racemic acids present in the same analytes were found to be 0.13–13.62%. This developed analytical method will be useful for the determination of chemical and enantiomeric purity of α-amino acids and/or esters as N-FMOC derivatives using amylose-derived CSPs.

Structure-guided engineering of: Meso -diaminopimelate dehydrogenase for enantioselective reductive amination of sterically bulky 2-keto acids

Cheng, Xinkuan,Chen, Xi,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming

, p. 4994 - 5002 (2018/10/17)

meso-Diaminopimelate dehydrogenase (DAPDH) and mutant enzymes are an excellent choice of biocatalysts for the conversion of 2-keto acids to the corresponding d-amino acids. However, their application in the enantioselective reductive amination of bulky 2-keto acids, such as phenylglyoxylic acid, 2-oxo-4-phenylbutyric acid, and indole-3-pyruvic acid, is still challenging. In this study, the structure-guided site-saturation mutagenesis of a Symbiobacterium thermophilum DAPDH (StDAPDH) gave rise to a double-site mutant W121L/H227I, which showed dramatically improved enzyme activities towards various 2-keto acids including these sterically bulky substrates. Several d-amino acids were prepared in optically pure form. The molecular docking of substrates into the active sites of wild-type and mutant W121L/H227I enzymes revealed that the substrate binding cavity of the mutant enzyme was reshaped to accommodate these bulky substrates, thus leading to higher enzyme activity. These results lay a foundation for further shaping the substrate binding pocket and manipulating the interactions between the substrate and binding sites to access highly active d-amino acid dehydrogenases for the preparation of synthetically challenging d-amino acids.

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