methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt

Base Information

• Chemical Name: methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt
• CAS No.: 130278-33-0
• Molecular Formula: C₄₃H₄₇NO₁₅S*2Na
• Molecular Weight: 895.889

Synonyms:

Chemical Property of methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt

There total 15 articles about methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (124751-19-5) → methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt (130278-33-0)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium hydride / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

2: methanol / Ambient temperature

3: 95 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 66 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2) 1,4-dioxane, 3 h, 80 deg C

5: 79 percent / 1,8-diazabicylo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2 h / Ambient temperature

6: 55 percent / activated powdered 4 Angstroem molecular sieve, BF₃*OEt₂ / toluene; CH₂Cl₂ / 4 h / -20 °C

7: 73 percent / pyridinium dichromate / dimethylformamide / 24 h / Ambient temperature

8: 78 percent / 24 h / Ambient temperature

9: 83 percent / sodium hydroxide / 1,2-dimethoxy-ethane; methanol / Ambient temperature

10: 1) sodium hydroxide, 2) sulfur trioxide-trimethylamine complex / 1) methanol-water, 1 h, room temperature, 2) N,N-dimethylformamide, 3 h, 60 deg C

With pyridine; methanol; sodium hydroxide; dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sulfur trioxide trimethylamine complex; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(90)84259-W

Reference yield:

benzyl bromide (100-39-0) → methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt (130278-33-0)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium hydride / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

2: methanol / Ambient temperature

3: 95 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 66 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2) 1,4-dioxane, 3 h, 80 deg C

5: 79 percent / 1,8-diazabicylo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2 h / Ambient temperature

6: 55 percent / activated powdered 4 Angstroem molecular sieve, BF₃*OEt₂ / toluene; CH₂Cl₂ / 4 h / -20 °C

7: 73 percent / pyridinium dichromate / dimethylformamide / 24 h / Ambient temperature

8: 78 percent / 24 h / Ambient temperature

9: 83 percent / sodium hydroxide / 1,2-dimethoxy-ethane; methanol / Ambient temperature

10: 1) sodium hydroxide, 2) sulfur trioxide-trimethylamine complex / 1) methanol-water, 1 h, room temperature, 2) N,N-dimethylformamide, 3 h, 60 deg C

With pyridine; methanol; sodium hydroxide; dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sulfur trioxide trimethylamine complex; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(90)84259-W

Reference yield:

(2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane (136656-50-3) → methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt (130278-33-0)

Guidance literature:

Multi-step reaction with 9 steps

1: methanol / Ambient temperature

2: 95 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 66 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2) 1,4-dioxane, 3 h, 80 deg C

4: 79 percent / 1,8-diazabicylo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2 h / Ambient temperature

5: 55 percent / activated powdered 4 Angstroem molecular sieve, BF₃*OEt₂ / toluene; CH₂Cl₂ / 4 h / -20 °C

6: 73 percent / pyridinium dichromate / dimethylformamide / 24 h / Ambient temperature

7: 78 percent / 24 h / Ambient temperature

8: 83 percent / sodium hydroxide / 1,2-dimethoxy-ethane; methanol / Ambient temperature

9: 1) sodium hydroxide, 2) sulfur trioxide-trimethylamine complex / 1) methanol-water, 1 h, room temperature, 2) N,N-dimethylformamide, 3 h, 60 deg C

With pyridine; methanol; sodium hydroxide; dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sulfur trioxide trimethylamine complex; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; In methanol; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(90)84259-W

upstream raw materials:

methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid

(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

benzyl bromide

(2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane

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