Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

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Chemical Name:Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate
CAS No.:444340-63-0
Molecular Formula:C₂₅H₃₈O₈SSi
Molecular Weight:526.723
Hs Code.:

Synonyms:Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

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Chemical Property of Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

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Technology Process of Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

There total 1 articles about Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate 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: 81.0%

: 98-59-9
p-toluenesulfonyl chloride

: 178939-00-9
(2E,6E)-(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-octa-2,6-dienedioic acid diethyl ester

: 444340-63-0
Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

Guidance literature:: With pyridine; In chloroform; at 20 ℃; for 72h;
DOI:10.1016/S0040-4020(02)00015-7

Reference yield: 72.0%

: 444340-63-0
Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

: 444340-64-1
diethyl (4R,5R)-4-hydroxy-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

Guidance literature:: With hydrogen fluoride; In water; acetonitrile; at 20 ℃; for 40h;
DOI:10.1016/S0040-4020(02)00015-7

Reference yield:

: 444340-63-0
Diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

: diethyl (4S,5R)-4-azido-5-(toluene-4-sulfonyloxy)-octa-2(E),6(E)-dienedioate

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / 40 percent aq. HF / acetonitrile; H₂O / 40 h / 20 °C

2: 48 percent / triphenylphosphine; hydrazoic acid; diethyl azodicarboxylate / tetrahydrofuran; benzene

With hydrogen azide; hydrogen fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; water; acetonitrile; benzene; 2: Mitsunobu reaction;
DOI:10.1016/S0040-4020(02)00015-7