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114869-95-3

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Basic Information
CAS No.: 114869-95-3
Name: a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate
Article Data: 3
Molecular Structure:
Molecular Structure of 114869-95-3 (a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate)
Formula: C24H29 N O8
Molecular Weight: 459.496
Synonyms: a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate
PSA: 112.55000
LogP: 2.55300
Related products
Synthetic route
2466-76-4

N-Acetylimidazole

87907-35-5

methyl 2--3-O-benzyl-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%
108-24-7

acetic anhydride

87907-35-5

methyl 2--3-O-benzyl-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;
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

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
1078691-95-8

(+)-D-glucosamine hydrochloride

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
501-53-1

benzyl chloroformate

PhMgX

PhMgX

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
87907-34-4

methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-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
60076-41-7

methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-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
4704-15-8

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

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
87907-35-5

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

75-36-5

acetyl chloride

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;
501-53-1

benzyl chloroformate

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
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