pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside

Base Information

• Chemical Name: pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside
• CAS No.: 441310-81-2
• Molecular Formula: C₄₈H₅₆O₆Si
• Molecular Weight: 757.055
• Mol file: 441310-81-2.mol

Synonyms:pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside

Chemical Property of pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside

There total 5 articles about pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-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: 85.0%

benzyl bromide (100-39-0) + pent-4-enyl 6-O-tert-butyldiphenylsilyl-D-glucopyranoside (441311-03-1) → pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside (441310-81-2)

Guidance literature:

With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; at 70 ℃; for 19h;

DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

pent-4-enyl α,β-D-glucopyranoside (182074-52-8) → pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside (441310-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / DBU / tetrahydrofuran / 22 h

2: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

With 18-crown-6 ether; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → pent-4-enyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucopyranoside (441310-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / DBU / tetrahydrofuran / 22 h

2: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

With 18-crown-6 ether; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00250-2

upstream raw materials:

benzyl bromide

pent-4-enyl 6-O-tert-butyldiphenylsilyl-D-glucopyranoside

n-Pent-4-enyl alcohol

pent-4-enyl α,β-D-glucopyranoside

Downstream raw materials:

N-acetyl-2,3,4-tri-O-benzyl-N-(benzyl N-benzyloxycarbonyl-L-β-aspartyl)-6-O-tert-butyldiphenylsilyl-α-D-glucopyranosylamine

[(2S,3R,4R,5S)-1-(2-Amino-ethyl)-3,4,5-tris-benzyloxy-piperidin-2-yl]-methanol

(2S,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

(2S,3R,4R,5R)-2,3,4-Tris-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-1,5-diol