(+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone

Base Information

• Chemical Name: (+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone
• CAS No.: 110826-71-6
• Molecular Formula: C₂₂H₃₂O₅S
• Molecular Weight: 408.559
• Mol file: 110826-71-6.mol

Synonyms:(+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone

Chemical Property of (+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone

There total 4 articles about (+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone 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: 64.0%

vinyllithium (917-57-7) → (+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone (110826-71-6) + C42H60O10S2

Guidance literature:

With CuCN; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

DOI:10.1021/ja00258a040

Reference yield: 18.0%

vinyllithium (917-57-7) + (-)-(4S)-4-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-2-butenolide (110826-70-5) → (+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone (110826-71-6) + C42H60O10S2

Guidance literature:

With CuCN; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

DOI:10.1021/ja00258a040

Reference yield:

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) → (+)-(2S,3R)-2-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-3-vinyl-γ-butirolactone (110826-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBr/NaBrO₃, 10percent HCl

2: 77 percent / pyridine / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) -20 deg C, 16 h

3: 64 percent / CuCN / diethyl ether; tetrahydrofuran / 1 h / -78 °C

With pyridine; hydrogenchloride; sodium bromate; sodium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja00258a040

upstream raw materials:

vinyllithium

(-)-(4S)-4-(((2,4,6-triisopropylbenzenesulfonyl)oxy)methyl)-2-butenolide

2,4,6-triisopropylphenylsulfonyl chloride

trisyl bromide