2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

Base Information

Chemical Name:2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide
CAS No.:1332641-33-4
Molecular Formula:C₃₅H₃₅BrO₄
Molecular Weight:599.565
Hs Code.:

Synonyms:2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

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Chemical Property of 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

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Technology Process of 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

There total 3 articles about 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide 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: 29.0%

: 99695-34-8
(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

: 1332641-35-6
2,3,4,6-tetra-O-benzyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosyl bromide

: 1332641-33-4
2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

Guidance literature:: (1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol; With carbon tetrabromide; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

With triphenylphosphine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1016/j.bmcl.2011.07.046

Reference yield:

: 1332641-35-6
2,3,4,6-tetra-O-benzyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosyl bromide

: 1332641-33-4
2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

Guidance literature:: With tetrabutylammomium bromide; In dichloromethane; optical yield given as %de;
DOI:10.1055/s-0030-1260801

Reference yield:

: 99695-34-8
(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

: 1332641-33-4
2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

Guidance literature:: Multi-step reaction with 2 steps

1: carbon tetrabromide; triphenylphosphine / chloroform / 0 - 20 °C

2: tetrabutylammomium bromide / dichloromethane

With carbon tetrabromide; tetrabutylammomium bromide; triphenylphosphine; In dichloromethane; chloroform; 1: Appel reaction;
DOI:10.1055/s-0030-1260801