(+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

Base Information

• Chemical Name: (+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane
• CAS No.: 256658-99-8
• Molecular Formula: C₁₆H₂₄O₄S
• Molecular Weight: 312.43
• Mol file: 256658-99-8.mol

Synonyms:(+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

Chemical Property of (+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

There total 6 articles about (+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)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: 76.0%

(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate (171523-69-6) → (+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane (256658-99-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 4h;

DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) → (+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane (256658-99-8)

Guidance literature:

Multi-step reaction with 5 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

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 / 5: Reduction;

DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

2,2-dimethoxy-propane (77-76-9) → (+)-[2S,4S,R(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane (256658-99-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; toluene; 1: Condensation / 2: Reduction;

DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

upstream raw materials:

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

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

2,2-dimethoxy-propane

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

Downstream raw materials:

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

3,5-dideoxy-2,4-O-(1-methylethylidene)-6-O-(phenylmethyl)-L-erythro-hexose

(4R,6S)-4-(2-(benzyloxy)ethyl)-6-ethynyl-2,2-dimethyl-1,3-dioxane

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