Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside

Base Information

• Chemical Name: Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside
• CAS No.: 303128-00-9
• Molecular Formula: C₅₆H₆₇NO₁₃Si
• Molecular Weight: 990.232
• Mol file: 303128-00-9.mol

Synonyms:Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside

Chemical Property of Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside

There total 21 articles about Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside 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: 92.0%

Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside (303127-98-2) → Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside (303128-00-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 20 ℃; for 1.5h;

DOI:10.1039/b002835p

Reference yield:

benzyl bromide (100-39-0) → Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside (303128-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 81 percent / TBAI / tetrahydrofuran / 5 h / 0 - 20 °C

2.1: methanol / 48 h

3.1: 2.45 g / imidazole / dimethylformamide / 0.67 h / 0 °C

4.1: 62 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

5.1: 92 percent / tributylstannane; azoisobutyronitrile / benzene / 1.5 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Metallation / 1.2: Etherification / 2.1: Substitution / 3.1: Substitution / 4.1: Substitution / 5.1: Reduction;

DOI:10.1039/b002835p

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside (303128-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.45 g / imidazole / dimethylformamide / 0.67 h / 0 °C

2: 62 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

3: 92 percent / tributylstannane; azoisobutyronitrile / benzene / 1.5 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tri-n-butyl-tin hydride; In dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: Substitution / 2: Substitution / 3: Reduction;

DOI:10.1039/b002835p

upstream raw materials:

Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

benzyl bromide

tert-butyldimethylsilyl chloride

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

Downstream raw materials:

(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside