methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Base Information

Chemical Name:methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate
CAS No.:256658-98-7
Molecular Formula:C₁₇H₂₄O₅S
Molecular Weight:340.441
Hs Code.:

Synonyms:methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

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Technology Process of methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

There total 4 articles about methyl (-)-[3S,5R,S(S)]-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: 97.0%

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

: 256658-97-6
methyl (-)-[3S,5R,S(S)]-syn-3,5-dihydroxy-6-(p-tolylsulfinyl)hexanoate

: 256658-98-7
methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 3h;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

: 91796-57-5
(1S,2R,5S,R_S)-(+)-Menthyl toluene-p-sulfinate

: 256658-98-7
methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 69 percent / NaH; tBuLi / pentane; tetrahydrofuran / 0.67 h / 0 °C

2: 47 percent / DIBAL-H / toluene; methanol / 1.75 h / -78 - 20 °C

3: 97 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 4 h / -78 °C

4: 97 percent / pTsOH / acetone / 3 h / 20 °C

With sodium tetrahydroborate; diethyl methoxy borane; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone; toluene; pentane; 1: Substitution / 2: Reduction / 3: Reduction / 4: Condensation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

: 218168-22-0
methyl (-)-(S)-3,5-dioxo-6-(p-tolylsulfinyl)hexanoate

: 256658-98-7
methyl (-)-[3S,5R,S(S)]-syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 47 percent / DIBAL-H / toluene; methanol / 1.75 h / -78 - 20 °C

2: 97 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 4 h / -78 °C

3: 97 percent / pTsOH / acetone / 3 h / 20 °C

With sodium tetrahydroborate; diethyl methoxy borane; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone; toluene; 1: Reduction / 2: Reduction / 3: Condensation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R