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114869-95-3

114869-95-3

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  • Qianyu Gold Product Factory Low Price Supplier of CAS114869-95-3 a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate Best Offer Manufacturer

    Cas No: 114869-95-3

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  • a-D-Glucopyranoside, methyl2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate 114869-95-3

    Cas No: 114869-95-3

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114869-95-3 Usage

General Description

The chemical a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate is a complex molecule derived from glucose. It consists of a glucose molecule with a methyl group at the 6-position and an acetate group at the 2-position. Additionally, it contains a 2-deoxy-2-[(phenylmethoxy)carbonyl]amino group at the 3-position and a phenylmethyl group at the 6-position. This chemical compound can be used in various pharmaceutical and chemical research applications, potentially as a glycosylation donor or as a substrate for enzymatic reactions. Its structural complexity suggests potential biological activity and may be of interest for further investigation in the field of medicinal chemistry.

Check Digit Verification of cas no

The CAS Registry Mumber 114869-95-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,4,8,6 and 9 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 114869-95:
(8*1)+(7*1)+(6*4)+(5*8)+(4*6)+(3*9)+(2*9)+(1*5)=153
153 % 10 = 3
So 114869-95-3 is a valid CAS Registry Number.

114869-95-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name [(2R,3S,4R,5R,6S)-3-hydroxy-6-methoxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)oxan-2-yl]methyl acetate

1.2 Other means of identification

Product number -
Other names -

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:114869-95-3 SDS

114869-95-3Synthetic route

N-Acetylimidazole
2466-76-4

N-Acetylimidazole

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside
87907-35-5

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
In dichloromethane Heating;59%
acetic anhydride
108-24-7

acetic anhydride

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside
87907-35-5

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
With pyridine In dichloromethane Acetylation;
2-carbobenzyloxyamino-2-deoxy-D-glucopyranose
3006-58-4, 13030-01-8, 42890-10-8, 42973-23-9, 77059-32-6, 121785-09-9, 7474-40-0

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: HCl
2: CSA / tetrahydrofuran
3: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
4: aq. AcOH
5: pyridine / CH2Cl2
View Scheme
(+)-D-glucosamine hydrochloride
1078691-95-8

(+)-D-glucosamine hydrochloride

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aq. Na2CO3
2: HCl
3: CSA / tetrahydrofuran
4: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
5: aq. AcOH
6: pyridine / CH2Cl2
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydrogencarbonate / water / 20 °C / Industry scale
1.2: 3 h / 20 °C / Industry scale
2.1: hydrogenchloride / 14 h / 60 - 65 °C / Industry scale
3.1: zinc(II) chloride / 24 h / 20 °C / Industry scale
4.1: potassium hydroxide / 1,4-dioxane / 4 h / Reflux; Industry scale
5.1: water; acetic acid / 90 - 100 °C / Industry scale
6.1: pyridine / dichloromethane / -55 - -50 °C / Inert atmosphere
View Scheme
benzyl chloroformate
501-53-1

benzyl chloroformate

PhMgX

PhMgX

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aq. Na2CO3
2: HCl
3: CSA / tetrahydrofuran
4: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
5: aq. AcOH
6: pyridine / CH2Cl2
View Scheme
methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside
87907-34-4

methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. AcOH
2: pyridine / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1: water; acetic acid / 90 - 100 °C / Industry scale
2: pyridine / dichloromethane / -55 - -50 °C / Inert atmosphere
View Scheme
methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside
60076-41-7

methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
2: aq. AcOH
3: pyridine / CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1: potassium hydroxide / 1,4-dioxane / 4 h / Reflux; Industry scale
2: water; acetic acid / 90 - 100 °C / Industry scale
3: pyridine / dichloromethane / -55 - -50 °C / Inert atmosphere
View Scheme
((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester
4704-15-8

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CSA / tetrahydrofuran
2: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
3: aq. AcOH
4: pyridine / CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: zinc(II) chloride / 24 h / 20 °C / Industry scale
2: potassium hydroxide / 1,4-dioxane / 4 h / Reflux; Industry scale
3: water; acetic acid / 90 - 100 °C / Industry scale
4: pyridine / dichloromethane / -55 - -50 °C / Inert atmosphere
View Scheme
methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside
87907-35-5

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

acetyl chloride
75-36-5

acetyl chloride

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
With pyridine In dichloromethane at -55 - -50℃; Inert atmosphere;
benzyl chloroformate
501-53-1

benzyl chloroformate

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydrogencarbonate / water / 20 °C / Industry scale
1.2: 3 h / 20 °C / Industry scale
2.1: hydrogenchloride / 14 h / 60 - 65 °C / Industry scale
3.1: zinc(II) chloride / 24 h / 20 °C / Industry scale
4.1: potassium hydroxide / 1,4-dioxane / 4 h / Reflux; Industry scale
5.1: water; acetic acid / 90 - 100 °C / Industry scale
6.1: pyridine / dichloromethane / -55 - -50 °C / Inert atmosphere
View Scheme
benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate
77059-32-6

benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogenchloride / 14 h / 60 - 65 °C / Industry scale
2: zinc(II) chloride / 24 h / 20 °C / Industry scale
3: potassium hydroxide / 1,4-dioxane / 4 h / Reflux; Industry scale
4: water; acetic acid / 90 - 100 °C / Industry scale
5: pyridine / dichloromethane / -55 - -50 °C / Inert atmosphere
View Scheme
C42H36O9S
1610791-08-6

C42H36O9S

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C60H59NO17

C60H59NO17

Conditions
ConditionsYield
With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride In dichloromethane at -60℃; Temperature; Solvent; Inert atmosphere;83%
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate
256348-52-4

2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate

Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-3-((2S,3R,4S,5R,6S)-3,5-diacetoxy-6-acetoxymethyl-4-benzyloxy-tetrahydro-pyran-2-yloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
256348-53-5

Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-3-((2S,3R,4S,5R,6S)-3,5-diacetoxy-6-acetoxymethyl-4-benzyloxy-tetrahydro-pyran-2-yloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Conditions
ConditionsYield
With tin(II) trifluoromethanesulfonate In dichloromethane at 0℃; Glycosidation;75%
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-D-xylopyranosyl fluoride
115195-88-5

2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-D-xylopyranosyl fluoride

Benzoic acid (2S,3R,4S,5R)-2-((2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4S,5R)-2-((2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Conditions
ConditionsYield
With 4 Angstroem molecular sives; boron trifluoride diethyl etherate In dichloromethane at -25℃; for 36h;48%
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-Α-D-xylopyranosyl fluoride
115195-82-9

2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-Α-D-xylopyranosyl fluoride

methyl 4-O-(2-O-acetyl-3-O-benzyl-4-o-levulinoyl-β-D-xylopyranosyl)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside
115203-89-9

methyl 4-O-(2-O-acetyl-3-O-benzyl-4-o-levulinoyl-β-D-xylopyranosyl)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
With 4 Angstroem molecular sives; boron trifluoride diethyl etherate In dichloromethane at -25℃; for 18h;40%
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

methyl 3-O-benzyl-4-O-monochloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate)
87907-09-3

methyl 3-O-benzyl-4-O-monochloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate)

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside
114869-96-4

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
With 2,6-lutidinium perchlorate 1) chlorobenzene, 20 min, reflux, 2) reflux, 15 min; Yield given. Multistep reaction;
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside
114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
Multi-step reaction with 2 steps
1: 1) 2,6-dimethylpyridinium perchlorate / 1) chlorobenzene, 20 min, reflux, 2) reflux, 15 min
2: 85 percent / 2,6-dimethylpyridine, hydrazinedithiocarbonate, acetic acid / methanol; CH2Cl2 / 0.17 h
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

(2R,3S,4R,5R,6R)-4-Benzyloxy-6-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-3-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4R,5R,6R)-4-Benzyloxy-6-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-3-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: Ag2O / acetonitrile
10: NaOMe / methanol
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6S)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6S)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((4aS,6S,7R,8R,8aR)-8-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
256348-54-6

[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((4aS,6S,7R,8R,8aR)-8-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6S)-3-((2R,3R,4S,5S,6R)-3-acetoxy-4-benzyloxy-6-formyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Acetic acid (2R,3S,4R,5R,6S)-3-((2R,3R,4S,5S,6R)-3-acetoxy-4-benzyloxy-6-formyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
256348-55-7

Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

(2R,3S,4S,5R,6R)-5-Acetoxy-6-((2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-3-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-5-Acetoxy-6-((2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-3-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: Ag2O / acetonitrile
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Acetic acid (4aS,6S,7R,8S,8aR)-6-((2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Acetic acid (4aS,6S,7R,8S,8aR)-6-((2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside
256486-94-9

methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C14H22NO17S2(3-)*3Na(1+)

C14H22NO17S2(3-)*3Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: Ag2O / acetonitrile
10: NaOMe / methanol
11: SO3*Py / dimethylformamide
12: NaOH / methanol
13: H2 / 10 percent Pd/C
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C14H21NO20S3(4-)*4Na(1+)

C14H21NO20S3(4-)*4Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: Ag2O / acetonitrile
10: NaOMe / methanol
11: SO3*Py / dimethylformamide
12: NaOH / methanol
13: H2 / 10 percent Pd/C
14: SO3*Py / H2O / pH 9.5
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

3-(3-azido-4-benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

3-(3-azido-4-benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
10: 89 percent / NaOMe; MeOH
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C36H40NO19S2(3-)*3Na(1+)

C36H40NO19S2(3-)*3Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: Ag2O / acetonitrile
10: NaOMe / methanol
11: SO3*Py / dimethylformamide
12: NaOH / methanol
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C20H32N2O24S3(4-)*4Na(1+)

C20H32N2O24S3(4-)*4Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
10: 89 percent / NaOMe; MeOH
11: SO3*Py / dimethylformamide / 20 °C
12: NaOH / methanol
13: H2 / 10 percent Pd/C
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
256348-59-1

5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C37H43NO19S2(2-)*2Na(1+)

C37H43NO19S2(2-)*2Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: Ag2O / acetonitrile
10: NaOMe / methanol
11: SO3*Py / dimethylformamide
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C20H30N2O30S5(6-)*6Na(1+)

C20H30N2O30S5(6-)*6Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
10: 89 percent / NaOMe; MeOH
11: SO3*Py / dimethylformamide / 20 °C
12: NaOH / methanol
13: H2 / 10 percent Pd/C
14: SO3*Py / dimethylformamide; H2O / pH 9.5
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C49H54N4O26S3(4-)*4Na(1+)

C49H54N4O26S3(4-)*4Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
10: 89 percent / NaOMe; MeOH
11: SO3*Py / dimethylformamide / 20 °C
12: NaOH / methanol
View Scheme
methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

C50H57N4O26S3(3-)*3Na(1+)

C50H57N4O26S3(3-)*3Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
9: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
10: 89 percent / NaOMe; MeOH
11: SO3*Py / dimethylformamide / 20 °C
View Scheme

114869-95-3Downstream Products

114869-95-3Relevant articles and documents

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

-

, (2013/02/28)

Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.

SYNTHESIS OF HEPARIN FRAGMENTS: A METHYL α-PENTANOSIDE WITH HIGH AFFINITY FOR ANTITHROMBIN III

Petitou, Maurice,Duchaussoy, Philippe,Lederman, Isidore,Choay, Jean,Jaquinet, Jean-Claude,et al.

, p. 67 - 76 (2007/10/02)

The synthesis is described of the methyl α-glycoside of the pentasaccharide which represents the sequence in heparin responsible for binding and activation of the anticoagulant protein Antithrombin III.It was obtained in a yield much better than that of the previously synthesized pentasaccharide and exhibited the same biological properties.

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