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a-D-Glucopyranoside, methyl4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate is a complex organic compound characterized by its unique structure that combines sugar and amino acid moieties. As a methylated glucopyranoside derivative, it features acetyl, methyl, phenylmethyl, and carbonyl groups, which contribute to its potential bioactivity and pharmaceutical applications.

114869-97-5

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114869-97-5 Usage

Uses

Used in Pharmaceutical Industry:
a-D-Glucopyranoside, methyl4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate is used as a bioactive compound for its potential pharmaceutical applications due to its unique structure and functional groups that may exhibit therapeutic effects.
Used in Drug Development:
a-D-Glucopyranoside, methyl4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate is utilized in drug development for its potential to interact with biological targets, given the presence of various substituents that may modulate its binding affinity and specificity.
Used in Medicinal Chemistry Research:
a-D-Glucopyranoside, methyl4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate serves as a subject of interest in medicinal chemistry research, where its structure can be further optimized for enhanced biological activity and selectivity towards specific therapeutic targets.

Check Digit Verification of cas no

The CAS Registry Mumber 114869-97-5 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 7 respectively.
Calculate Digit Verification of CAS Registry Number 114869-97:
(8*1)+(7*1)+(6*4)+(5*8)+(4*6)+(3*9)+(2*9)+(1*7)=155
155 % 10 = 5
So 114869-97-5 is a valid CAS Registry Number.

114869-97-5SDS

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 Methyl 6-O-acetyl-4-O-(2-O-acetyl-3-O-benzyl-6-methyl-α-L-idopyra nuronosyl)-3-O-benzyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-α-D- glucopyranoside

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:114869-97-5 SDS

114869-97-5Synthetic route

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

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
With 2,6-dimethylpyridine; dithiocarbonic acid hydrazide; acetic acid In methanol; dichloromethane for 0.166667h;85%
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

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

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
Esterification;
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-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 13 steps
1: HCl
2: CSA / tetrahydrofuran
3: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
4: aq. AcOH
5: pyridine / CH2Cl2
6: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
7: NaOMe; MeOH
8: CSA / acetone
9: DMAP; pyridine / CH2Cl2
10: aq. AcOH
11: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
12: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
(+)-D-glucosamine hydrochloride
1078691-95-8

(+)-D-glucosamine hydrochloride

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 14 steps
1: aq. Na2CO3
2: HCl
3: CSA / tetrahydrofuran
4: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
5: aq. AcOH
6: pyridine / CH2Cl2
7: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
8: NaOMe; MeOH
9: CSA / acetone
10: DMAP; pyridine / CH2Cl2
11: aq. AcOH
12: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
13: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
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

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 9 steps
1: pyridine / CH2Cl2
2: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
3: NaOMe; MeOH
4: CSA / acetone
5: DMAP; pyridine / CH2Cl2
6: aq. AcOH
7: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
8: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
Multi-step reaction with 3 steps
1: 59 percent / CH2Cl2 / Heating
2: 1) 2,6-dimethylpyridinium perchlorate / 1) chlorobenzene, 20 min, reflux, 2) reflux, 15 min
3: 85 percent / 2,6-dimethylpyridine, hydrazinedithiocarbonate, acetic acid / methanol; CH2Cl2 / 0.17 h
View Scheme
benzyl chloroformate
501-53-1

benzyl chloroformate

PhMgX

PhMgX

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 14 steps
1: aq. Na2CO3
2: HCl
3: CSA / tetrahydrofuran
4: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
5: aq. AcOH
6: pyridine / CH2Cl2
7: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
8: NaOMe; MeOH
9: CSA / acetone
10: DMAP; pyridine / CH2Cl2
11: aq. AcOH
12: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
13: 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

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 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-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 10 steps
1: aq. AcOH
2: pyridine / CH2Cl2
3: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
4: NaOMe; MeOH
5: CSA / acetone
6: DMAP; pyridine / CH2Cl2
7: aq. AcOH
8: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
9: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
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-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 11 steps
1: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
2: aq. AcOH
3: pyridine / CH2Cl2
4: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
5: NaOMe; MeOH
6: CSA / acetone
7: DMAP; pyridine / CH2Cl2
8: aq. AcOH
9: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
10: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
[(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

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 6 steps
1: CSA / acetone
2: DMAP; pyridine / CH2Cl2
3: aq. AcOH
4: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
5: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
[(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

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 5 steps
1: DMAP; pyridine / CH2Cl2
2: aq. AcOH
3: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
4: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
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

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 2 steps
1: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
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

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 3 steps
1: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
2: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
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

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 4 steps
1: aq. AcOH
2: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
3: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
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

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 7 steps
1: NaOMe; MeOH
2: CSA / acetone
3: DMAP; pyridine / CH2Cl2
4: aq. AcOH
5: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
6: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
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-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 12 steps
1: CSA / tetrahydrofuran
2: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
3: aq. AcOH
4: pyridine / CH2Cl2
5: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
6: NaOMe; MeOH
7: CSA / acetone
8: DMAP; pyridine / CH2Cl2
9: aq. AcOH
10: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
11: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
benzoyl chloride
98-88-4

benzoyl chloride

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

C47H51NO16

C47H51NO16

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 10h; Cooling with ice;95%
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

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose
241129-78-2

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose

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
With 4 A molecular sieve; t-butyldimethylsiyl triflate In toluene at -20℃; Glycosidation;88%
4-methoxybenzyl 2,2,2-trichloroacetimidate

4-methoxybenzyl 2,2,2-trichloroacetimidate

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

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-p-methoxybenzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside
155630-80-1

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

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In diethyl ether; dichloromethane at 20℃; for 0.5h;85%
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

Acetic acid (2R,3S,4R,5R)-2-acetoxymethyl-5-azido-3-methoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,5R)-2-acetoxymethyl-5-azido-3-methoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

5-acetoxy-3-(4-acetoxy-6-acetoxymethyl-3-azido-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

5-acetoxy-3-(4-acetoxy-6-acetoxymethyl-3-azido-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
With 4 A molecular sieve; t-butyldimethylsiyl triflate In toluene at -20℃; Glycosidation;76%
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

3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-glucopyranosyluronate)-α-D-glucopyranosyl bromide

3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-glucopyranosyluronate)-α-D-glucopyranosyl bromide

C73H83ClN4O28

C73H83ClN4O28

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate In 1,2-dichloro-ethane41%
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

methyl iodide
74-88-4

methyl iodide

(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
With silver(l) oxide In acetonitrile Methylation;
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

(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 2 steps
1: Ag2O / acetonitrile
2: NaOMe / methanol
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Ag2O / acetonitrile
2: NaOMe / methanol
3: SO3*Py / dimethylformamide
4: NaOH / methanol
5: H2 / 10 percent Pd/C
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Ag2O / acetonitrile
2: NaOMe / methanol
3: SO3*Py / dimethylformamide
4: NaOH / methanol
5: H2 / 10 percent Pd/C
6: SO3*Py / H2O / pH 9.5
View Scheme
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

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 2 steps
1: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
2: 89 percent / NaOMe; MeOH
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Ag2O / acetonitrile
2: NaOMe / methanol
3: SO3*Py / dimethylformamide
4: NaOH / methanol
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
2: 89 percent / NaOMe; MeOH
3: SO3*Py / dimethylformamide / 20 °C
4: NaOH / methanol
5: H2 / 10 percent Pd/C
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Ag2O / acetonitrile
2: NaOMe / methanol
3: SO3*Py / dimethylformamide
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
2: 89 percent / NaOMe; MeOH
3: SO3*Py / dimethylformamide / 20 °C
4: NaOH / methanol
5: H2 / 10 percent Pd/C
6: SO3*Py / dimethylformamide; H2O / pH 9.5
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
2: 89 percent / NaOMe; MeOH
3: SO3*Py / dimethylformamide / 20 °C
4: NaOH / methanol
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C
2: 89 percent / NaOMe; MeOH
3: SO3*Py / dimethylformamide / 20 °C
View Scheme

114869-97-5Upstream product

114869-97-5Relevant academic research and scientific papers

Synthesis of heparin partial structures and their binding activities to platelets

Koshida, Shuhei,Suda, Yasuo,Sobel, Michael,Ormsby, Julie,Kusumoto, Shoichi

, p. 3127 - 3132 (2007/10/03)

A synthetic pentasaccharide corresponding to the antithrombin III-binding region in heparin was also found to bind to human platelets. To identify the platelet-binding site in the pentasaccharide which is expected to be a novel sequence in heparin responsible for its platelet-binding, five partial structures of this particular pentasaccharide were synthesized. In a competitive assay using [3H]-heparin, a trisaccharide, O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)- (1→4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1→4)-2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranose, was concluded to be a high-affinity site for heparin's binding to platelets.

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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