3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose
• CAS No.: 17231-20-8
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331
• Mol file: 17231-20-8.mol

Synonyms:3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

There total 6 articles about 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose 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: 94.0%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + di(n-butyl)tin oxide (818-08-6) → 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (17231-20-8)

Guidance literature:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol; di(n-butyl)tin oxide; With 3 A molecular sieve; In methanol; toluene; for 3h; Heating;

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In chloroform; for 0.0833333h;

DOI:10.1016/S0008-6215(99)00032-4

Reference yield: 90.0%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (17231-20-8)

Guidance literature:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol; With di(n-butyl)tin oxide; In toluene; Reflux;

With N-Bromosuccinimide; In chloroform; for 0.0833333h; regioselective reaction;

DOI:10.1002/ejoc.200800763

Reference yield: 77.0%

N-Bromosuccinimide (128-08-5) + (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (17231-20-8)

Guidance literature:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol; With di(n-butyl)tin oxide; In toluene; at 120 ℃; for 6h;

N-Bromosuccinimide; In chloroform; at 20 ℃; for 0.0833333h;

DOI:10.1007/s00706-009-0171-1

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

di(n-butyl)tin oxide

N-Bromosuccinimide

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

C₁₇H₂₂N₂O₅

5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

ethyl 3-O-benzyl-5,6-dideoxy-5-C-hydroxymethyl-1,2-isopropylidene-α-D-xylo-hept-5-(E)-enofuranuronate

4-(3-O-benzyl-1,2-O-isopropylidene-α-D-threo-furanos-4-yl)pyridazin-6-one

Refernces

• 1、 Silva, Sandrina,Sanchez-Fernandez, Elena M.,Ortiz Mellet, Carmen,Tatibouet, Arnaud,Pilar Rauter, Amelia,Rollin, Patrick. "N-Thiocarbonyl iminosugars: Synthesis and evaluation of castanospermine analogues bearing oxazole-2(3H)-thione moieties". . p. 7941 - 7951. Retrieved 2014/01/06.
• 2、 Xavier, Nuno M.,Silva, Sandrina,Madeira, Paulo J. A.,Helena Florencio,Silva, Filipa V. M.,Justino, Jorge,Thiem, Joachim,Rauter, Amelia P.. "Synthesis and biological evaluation of sugars containing α,β-unsaturated γ-lactones". experimental part. p. 6134 - 6143. Retrieved 2009/05/31.