(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

Base Information

Chemical Name:(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester
CAS No.:56703-53-8
Molecular Formula:C₂₉H₃₂O₆
Molecular Weight:476.569
Hs Code.:

Synonyms:(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

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Chemical Property of (Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

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Technology Process of (Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

There total 4 articles about (Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester 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: 60.0%

: 89361-52-4
2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranose

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 56703-53-8
(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

: 56703-54-9
methyl (4S,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-2-enoate

Guidance literature:: With benzoic acid; In acetonitrile; for 0.833333h; Reflux;
DOI:10.3987/COM-11-12263

Reference yield:

: 50-69-1
D-ribose

: 100-39-0
benzyl bromide

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 56703-53-8
(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

: 56703-54-9
methyl (4S,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-2-enoate

: methyl (4S,5S,6R)-4,5,6-tris(benzyloxy)-7-hydroxyhept-2-enoate

: methyl (4S,5S,6R)-4,5,6-tris(benzyloxy)-7-hydroxyhept-2-enoate

Guidance literature:: D-ribose; With hydrogenchloride; In methanol; for 4h; Inert atmosphere; Reflux;

benzyl bromide; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 48h;

methyl (triphenylphosphoranylidene)acetate; Overall yield = 2.58 g; Further stages;
DOI:10.1016/j.tet.2020.131397

Reference yield:

: 50-69-1
D-ribose

: 100-39-0
benzyl bromide

: 18162-48-6
tert-butyldimethylsilyl chloride

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 56703-53-8
(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

: 56703-54-9
methyl (4S,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-2-enoate

: Methyl (4S,5S,6R)-4,5,6-tris(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)hept-2-enoate

: C₃₅H₄₆O₆Si

Guidance literature:: D-ribose; With hydrogenchloride; In methanol; for 4h; Inert atmosphere; Reflux;

benzyl bromide; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 48h;

tert-butyldimethylsilyl chloride; methyl (triphenylphosphoranylidene)acetate; Further stages;
DOI:10.1016/j.tet.2020.131397