ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 128716-38-1
• Molecular Formula: C₃₂H₃₈O₅S
• Molecular Weight: 534.717
• Mol file: 128716-38-1.mol

Synonyms:ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

There total 3 articles about ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 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: 91.0%

(2S,3R,4S,5R,6R)-4-Allyloxy-2-ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol (128716-37-0) + benzyl bromide (100-39-0) → ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (128716-38-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(89)85090-6

Reference yield:

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside (39698-00-5) → ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (128716-38-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / freshly fused ZnCl₂, molecular sieves (4 Angstroem) / CH₂Cl₂ / 0.25 h

2: 97 percent / sodium methoxide / methanol / 18 h

3: 91 percent / sodium hydride / dimethylformamide / 2 h / Ambient temperature

With 4 A molecular sieve; sodium methylate; sodium hydride; zinc(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)85090-6

Reference yield:

ethyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside (128716-36-9) → ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (128716-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / sodium methoxide / methanol / 18 h

2: 91 percent / sodium hydride / dimethylformamide / 2 h / Ambient temperature

With sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)85090-6

upstream raw materials:

(2S,3R,4S,5R,6R)-4-Allyloxy-2-ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

benzyl bromide

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

ethyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

3-N-benzyloxycarbonylaminopropyl 3-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside

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

O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose

Benzyl 2,4-di-O-benzyl-3-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-L-rhamnopyranoside