(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Base Information

Chemical Name:(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate
CAS No.:171523-69-6
Molecular Formula:C₁₇H₂₄O₅S
Molecular Weight:340.441
Hs Code.:

Synonyms:(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

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Chemical Property of (+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

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Technology Process of (+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

There total 8 articles about (+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate 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: 98.0%

: 77-76-9
2,2-dimethoxy-propane

: 171523-68-5
(+)-<3(R),5(S),S(R)> methyl 3,5-dihydroxy-6-(p-tolylsulfinyl) hexanoate

: 171523-69-6
(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Guidance literature:: With toluene-4-sulfonic acid; toluene-4-sulfonic acid; In acetone; for 3h; Ambient temperature;
DOI:10.1021/jo00129a018

Reference yield:

: 1517-82-4
(-)-menthyl p-toluenesulfinate

: 171523-69-6
(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) a) NaH, b) t-BuLi / 1.) THF, pentane, a) 0 deg C, 15 min, b) 0 deg C, 2.) THF, pentane, 0 deg C, 2 h

2: 44 percent / DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

3: 90 percent / NaBH₄, Et₂BOMe / tetrahydrofuran; methanol / 5.75 h / -78 °C

4: 94 percent / p-TsOH / acetone / 12 h / Ambient temperature

With sodium tetrahydroborate; diethyl methoxy borane; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone; toluene;
DOI:10.1016/0957-4166(96)00292-3

Reference yield:

: 171523-67-4
(+)-<5(S),S(R)> methyl 3-oxo-5-hydroxy-6-(p-tolylsulfinyl) hexanoate

: 171523-69-6
(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / NaBH₄, Et₂BOMe / tetrahydrofuran; methanol / 5.75 h / -78 °C

2: 94 percent / p-TsOH / acetone / 12 h / Ambient temperature

With sodium tetrahydroborate; diethyl methoxy borane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone;
DOI:10.1016/0957-4166(96)00292-3