Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside

Base Information

• Chemical Name: Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside
• CAS No.: 344551-05-9
• Molecular Formula: C₅₈H₆₁ClO₁₄
• Molecular Weight: 1017.57
• Mol file: 344551-05-9.mol

Synonyms:Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside

Chemical Property of Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside

There total 15 articles about Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-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: 63.0%

Benzyl 2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside (344550-93-2) + Pent-4-enyl 6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranoside (344550-96-5) → Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside (344551-05-9)

Guidance literature:

With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -20 ℃;

DOI:10.1039/b006981g

Reference yield:

β-D-galactose peracetate (4163-60-4) → Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside (344551-05-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

2.1: 12.4 g / NaOMe; MeOH / 2 h

3.1: 12.4 g / CSA / CHCl₃ / 1 h / Heating

4.1: NaH / dimethylformamide / 0.5 h / 20 °C

4.2: 16.8 g / Bu₄NI / dimethylformamide

5.1: 13.6 g / PTSA; propane-1,3-diol / CH₂Cl₂; methanol / 96 h / Heating

6.1: pyridine / 6 h / 20 °C

7.1: NaH / dimethylformamide

7.2: 3.37 g / dimethylformamide / 16 h

8.1: 63 percent / NIS; TESOTf / CH₂Cl₂ / -20 °C

With pyridine; methanol; N-iodo-succinimide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; triethylsilyl trifluoromethyl sulfonate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; trimethyleneglycol; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1039/b006981g

Reference yield:

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside (74801-06-2) → Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside (344551-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / 6 h / 20 °C

2.1: NaH / dimethylformamide

2.2: 3.37 g / dimethylformamide / 16 h

3.1: 63 percent / NIS; TESOTf / CH₂Cl₂ / -20 °C

With pyridine; N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b006981g

upstream raw materials:

Benzyl 2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside

Pent-4-enyl 6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranoside

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside

benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Downstream raw materials:

Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside