Acetic acid phenylsulfanyl-((4S,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester

Base Information

• Chemical Name: Acetic acid phenylsulfanyl-((4S,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester
• CAS No.: 81769-42-8
• Molecular Formula: C₁₉H₂₆O₆S
• Molecular Weight: 382.478
• Mol file: 81769-42-8.mol

Synonyms:

Chemical Property of Acetic acid phenylsulfanyl-((4S,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid phenylsulfanyl-((4S,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester

There total 8 articles about Acetic acid phenylsulfanyl-((4S,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl 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:

((2S,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol (80581-19-7) → Acetic acid phenylsulfanyl-((4S,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester (81769-42-8,81769-43-9,81769-44-0,81769-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / 2-methyl-propan-2-ol / 3 h / 100 °C

2: 1.) camphorsulfonic acid, 2.) m-CPBA, 3.) NaOAc

With sodium hydroxide; camphor-10-sulfonic acid; sodium acetate; 3-chloro-benzenecarboperoxoic acid; In tert-butyl alcohol;

DOI:10.1021/ja00376a050

Reference yield:

((2R,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol (80532-36-1) → Acetic acid phenylsulfanyl-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester (81769-42-8,81769-43-9,81769-44-0,81769-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / 2-methyl-propan-2-ol / 3 h / 100 °C

2: 1.) camphorsulfonic acid, 2.) m-CPBA, 3.) NaOAc

With sodium hydroxide; camphor-10-sulfonic acid; sodium acetate; 3-chloro-benzenecarboperoxoic acid; In tert-butyl alcohol;

DOI:10.1021/ja00376a050

Reference yield:

(S)-4,5-isopropylidenedioxy-2-pentenol (146986-66-5) → Acetic acid phenylsulfanyl-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester (81769-42-8,81769-43-9,81769-44-0,81769-45-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Ti(O-i-Pr)4, (-)-DET, TBHP / CH₂Cl₂ / 15 h / -20 °C

2: NaOH / 2-methyl-propan-2-ol / 3 h / 100 °C

3: 1.) camphorsulfonic acid, 2.) m-CPBA, 3.) NaOAc

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; camphor-10-sulfonic acid; sodium acetate; (-)-diethyl tartrate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja00376a050

upstream raw materials:

2-methyl-1,2-epoxypropane

acetic anhydride

(2R,3S,4R)-5-(Phenylthio)-1,2-O-isopropylidenepentane-1,2,3,4-tetrol

((2R,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol

Downstream raw materials:

2,3:4,5-di-O-isopropylidene-D-arabinitol

((4S,4’R,5S)-2,2,2’,2’-tetramethyl-[4,4’-bi(1,3-dioxolan)]-5-yl)methanol

2,3,4,5-di-O-isopropylidene-D-xylose aldehyde

(4S,4'R,5S)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolane)]-5-carbaldehyde