ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside
• CAS No.: 172275-99-9
• Molecular Formula: C₂₉H₃₂O₅S
• Molecular Weight: 492.636
• Mol file: 172275-99-9.mol

Synonyms:ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside

Chemical Property of ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside

There total 5 articles about ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-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: 93.0%

benzyl bromide (100-39-0) + ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (131564-36-8) → ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside (172275-99-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 2.5h;

DOI:10.1039/d0ob01640c

Reference yield: 42.0%

benzyl bromide (100-39-0) + ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (131564-36-8) → ethyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside + ethyl 3-O-phenylmethyl-4:6-O-phenylmethylene-1-thio-β-D-galactopyranoside + ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside (172275-99-9)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; for 88h; Heating;

Reference yield:

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (55722-49-1) → ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside (172275-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate / methanol; dichloromethane / 0.5 h / 20 °C / pH Ca_. 9

2: camphor-10-sulfonic acid / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

3: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2.5 h / 0 °C

With camphor-10-sulfonic acid; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1039/d0ob01640c

upstream raw materials:

benzyl bromide

ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

β-D-galactose peracetate

Downstream raw materials:

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