Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester

Base Information

Chemical Name:Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester
CAS No.:204327-31-1
Molecular Formula:C₂₄H₄₂O₇SSi
Molecular Weight:502.745
Hs Code.:

Synonyms:Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester

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Chemical Property of Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester

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Technology Process of Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester

There total 9 articles about Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl 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: 93.0%

: 124-63-0
methanesulfonyl chloride

: 204327-30-0
(E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

: 204327-31-1
Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.666667h;
DOI:10.1021/jo972187r

Reference yield:

: 53346-05-7,41954-96-5,81445-44-5,81445-45-6
(R)-2-benzyloxypropanal

: 204327-31-1
Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) THF, -40 deg C, 40 min, 2.) THF, room temp., 20 h

2: DIBAL, ZnBr₂

3: 90 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

4: 99 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Ambient temperature

5: 94 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

6: 93 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

With 1H-imidazole; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc dibromide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo972187r

Reference yield:

: 100-39-0
benzyl bromide

: 204327-31-1
Methanesulfonic acid (E)-(1S,2S,5R)-5-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methoxymethoxy-hex-3-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / Ag₂O / diethyl ether / Heating

2: 96 percent / DIBAL / diethyl ether; pentane; hexane / 0.5 h / -78 °C

3: 1.) NaH / 1.) THF, -40 deg C, 40 min, 2.) THF, room temp., 20 h

4: DIBAL, ZnBr₂

5: 90 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

6: 99 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Ambient temperature

7: 94 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

8: 93 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

With 1H-imidazole; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; zinc dibromide; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo972187r