(+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane

Base Information

Chemical Name:(+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane
CAS No.:256659-01-5
Molecular Formula:C₂₅H₃₂O₅S
Molecular Weight:444.592
Hs Code.:

Synonyms:(+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane

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Chemical Property of (+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane

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Technology Process of (+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane

There total 8 articles about (+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane 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: 86.0%

: 108-24-7
acetic anhydride

: 256659-00-4
(+)-[2S,4S,S(R)]-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

: 256659-01-5
(+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane

Guidance literature:: With sodium acetate; at 20 - 135 ℃; for 12h;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

: 1517-82-4
(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

: 256659-01-5
(+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane

Guidance literature:: Multi-step reaction with 7 steps

1: 68 percent / NaH; tBuLi / pentane; tetrahydrofuran / 0.67 h / 0 °C

2: 44 percent / DIBAL-H / toluene; methanol / 1.75 h / -78 - 20 °C

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

4: 98 percent / pTsOH / acetone / 3 h / 20 °C

5: 76 percent / DIBAL-H / toluene; tetrahydrofuran / 4 h / -78 °C

6: 55 percent / Bu₄NI / tetrahydrofuran / 20 °C

7: 86 percent / NaOAc / 12 h / 20 - 135 °C

With sodium tetrahydroborate; diethyl methoxy borane; tert.-butyl lithium; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone; toluene; pentane; 1: Substitution / 2: Reduction / 3: Reduction / 4: Condensation / 5: Reduction / 6: benzylation / 7: Acetylation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

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

: 256659-01-5
(+)-(2S,4S)-1-acetoxy-6-benzyloxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylthio)hexane

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / pTsOH / acetone / 3 h / 20 °C

2: 76 percent / DIBAL-H / toluene; tetrahydrofuran / 4 h / -78 °C

3: 55 percent / Bu₄NI / tetrahydrofuran / 20 °C

4: 86 percent / NaOAc / 12 h / 20 - 135 °C

With sodium acetate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; toluene; 1: Condensation / 2: Reduction / 3: benzylation / 4: Acetylation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R