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

Base Information

• Chemical Name: ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• CAS No.: 213459-71-3
• Molecular Formula: C₂₅H₃₂O₅S
• Molecular Weight: 444.592
• Mol file: 213459-71-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-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: 73.0%

benzyl bromide (100-39-0) + ethyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (172146-95-1) → ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (213459-71-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1.5h;

DOI:10.1016/S0008-6215(98)00087-1

Reference yield:

ethyl 1-thio-β-D-galactopyranoside (56245-60-4,686299-00-3) → ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (213459-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) p-toluenesulfonic acid; 2.) 50percent aq. CF₃CO₂H / 1.) DMF, overnight; 2.) CH₂Cl₂, 10 min

2: 73 percent / NaH / dimethylformamide / 1.5 h

With sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00087-1

Reference yield: 96.0%

ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (213459-71-3) → ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside (215371-44-1)

Guidance literature:

With acetic acid; at 60 ℃; for 1h;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

upstream raw materials:

benzyl bromide

ethyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

ethyl 1-thio-β-D-galactopyranoside

Downstream raw materials:

ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside

5-azidopentyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside

3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

ethyl 2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside