benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

Base Information

Chemical Name:benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside
CAS No.:185380-71-6
Molecular Formula:C₄₈H₅₂O₉
Molecular Weight:772.935
Hs Code.:

Synonyms:benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

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Chemical Property of benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

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Technology Process of benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

There total 12 articles about benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside 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: 7.0%

: 3-O-allyl-2,5-di-O-benzyl-L-arabinofuranose

: 185380-63-6
benzyl 2,4-di-O-benzyl-α-D-xylopyranoside

: 185380-71-6
benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

: benzyl O-(3-O-allyl-2,5-di-O-benzyl-β-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

Guidance literature:: With trimethylsilyl bromide; 3 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide; In dichloromethane; Ambient temperature;
DOI:10.1246/bcsj.69.3247

Reference yield:

: 100-44-7
benzyl chloride

: 185380-71-6
benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / KOH / 1.5 h / 120 °C

2: 79 percent / aq. H₂SO₄, AcOH / 1.5 h / 75 °C

3: 52 percent / trimethylsilyl bromide, CoBr₂, tetrabutylammonium bromide, molecular sieves 3A / CH₂Cl₂ / Ambient temperature

With potassium hydroxide; trimethylsilyl bromide; 3 A molecular sieve; sulfuric acid; tetrabutylammomium bromide; acetic acid; cobalt(II) bromide; In dichloromethane;
DOI:10.1246/bcsj.69.3247

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 185380-71-6
benzyl O-(3-O-allyl-2,5-di-O-benzyl-α-L-arabinofuranosyl)-(1-3)-2,4-di-O-benzyl-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) pTsOH*H₂O, 2.) Et₃N / 1.) 70 deg C, 60 min, 2.) CHCl₃, RT

2: 64 percent / NaH / 1 h / 100 °C

3: 52 percent / trimethylsilyl bromide, CoBr₂, tetrabutylammonium bromide, molecular sieves 3A / CH₂Cl₂ / Ambient temperature

With trimethylsilyl bromide; 3 A molecular sieve; tetrabutylammomium bromide; sodium hydride; toluene-4-sulfonic acid; triethylamine; cobalt(II) bromide; In dichloromethane;
DOI:10.1246/bcsj.69.3247