(1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Base Information

• Chemical Name: (1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate
• CAS No.: 1000050-97-4
• Molecular Formula: C₁₅H₂₀O₆S
• Molecular Weight: 328.386
• Mol file: 1000050-97-4.mol

Synonyms:(1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Chemical Property of (1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

There total 5 articles about (1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate 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%

(3R,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-methyldihydrofuran-2(3H)-one (1000050-95-2) + methanesulfonyl chloride (124-63-0) → (1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate (1000050-97-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3h;

Reference yield:

5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-methyldihydrofuran-2(3H)-one + methanesulfonyl chloride (124-63-0) → (1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate (1000050-97-4) + (1R)-2-(benzyloxy)-1-[4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3h; Overall yield = 97 %; Overall yield = 9.9 g;

DOI:10.1016/j.bmc.2013.03.022

Reference yield:

(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoic acid (127949-92-2) → (1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate (1000050-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra(n-butyl)ammonium hydrogensulfate; Shi's ketone; Oxone; potassium carbonate; edetate disodium / acetonitrile / 9 h / 0 °C

2: triethylamine / dichloromethane / 3 h / 0 °C

With Oxone; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate; triethylamine; In dichloromethane; acetonitrile; 1: |Shi Asymmetric Epoxidation;

DOI:10.1016/j.bmc.2013.03.022

upstream raw materials:

(3R,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-methyldihydrofuran-2(3H)-one

methanesulfonyl chloride

(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoic acid

(4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one

Downstream raw materials:

(3R,5S)-5-[(1S)-1-azido-2-(benzyloxy)ethyl]-3-methyldihydrofuran-2(3H)-one