(4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene

Base Information

Chemical Name:(4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene
CAS No.:307315-83-9
Molecular Formula:C₃₅H₄₇ClO₇SSi
Molecular Weight:675.358
Hs Code.:

Synonyms:(4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene

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Chemical Property of (4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene

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Technology Process of (4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene

There total 7 articles about (4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene 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: 100.0%

: 3518-65-8
monochloromethanesulfonyl chloride

: 307315-82-8
(4R,5S,6S)-1-tert-butyldimethylsilyloxy-4,5,7-tribenzyloxy-2(E)-hepten-6-ol

: 307315-83-9
(4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene

Guidance literature:: With pyridine; at 20 ℃; for 0.5h;
DOI:10.1016/S0968-0896(00)00170-X

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 307315-83-9
(4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / Et₃N; DMAP / dimethylformamide / 1 h / 20 °C

2: 97 percent / Py / 0.5 h / 20 °C

3: 75 percent / 18-crown-6 / toluene / Heating

4: 97 percent / NaOMe / methanol / 1 h / 20 °C

5: 100 percent / Py / 0.5 h / 20 °C

With pyridine; dmap; 18-crown-6 ether; sodium methylate; triethylamine; In methanol; N,N-dimethyl-formamide; toluene; 1: silylation / 2: Substitution / 3: Substitution / 4: Deacetylation / 5: Substitution;
DOI:10.1016/S0968-0896(00)00170-X

Reference yield:

: 307315-77-1
methyl (4R,5S,6R)-6-hydroxy-4,5,7-tribenzyloxy-2(E)-heptenoate

: 307315-83-9
(4R,5S,6S)-1-tert-butyldimethylsilyloxy-6-[(chloro-methylsulfonyl)-oxy]-4,5,7-tribenzyloxy-2(E)-heptene

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / DIBAL / hexane; CH₂Cl₂ / 0.5 h / 0 °C

2: 98 percent / Et₃N; DMAP / dimethylformamide / 1 h / 20 °C

3: 97 percent / Py / 0.5 h / 20 °C

4: 75 percent / 18-crown-6 / toluene / Heating

5: 97 percent / NaOMe / methanol / 1 h / 20 °C

6: 100 percent / Py / 0.5 h / 20 °C

With pyridine; dmap; 18-crown-6 ether; sodium methylate; diisobutylaluminium hydride; triethylamine; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Reduction / 2: silylation / 3: Substitution / 4: Substitution / 5: Deacetylation / 6: Substitution;
DOI:10.1016/S0968-0896(00)00170-X