(4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester

Base Information

• Chemical Name: (4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester
• CAS No.: 688797-19-5
• Molecular Formula: C₂₂H₂₈O₈S₂
• Molecular Weight: 484.592
• Mol file: 688797-19-5.mol

Synonyms:(4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester

Chemical Property of (4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester

There total 3 articles about (4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl 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: 70.0%

methanesulfonyl chloride (124-63-0) + (2R,4S)-2,5-bis(benzyloxy)-3-methylenepentane-1,4-diol (688797-18-4) → (4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester (688797-19-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo035735b

Reference yield:

2,5-di-O-benzyl-3-deoxy-3-methylene-D-erythro-pentofuranose → (4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester (688797-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium borohydride / tetrahydrofuran

2: pyridine / CH₂Cl₂

With pyridine; lithium borohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1081/NCN-200060072

Reference yield:

methyl 2,5-di-O-benzyl-3-deoxy-3-methylene-D-erythro-pentofuranoside → (4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester (688797-19-5)

Guidance literature:

Multi-step reaction with 3 steps

1: HCl / dioxane

2: lithium borohydride / tetrahydrofuran

3: pyridine / CH₂Cl₂

With pyridine; hydrogenchloride; lithium borohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1081/NCN-200060072

upstream raw materials:

methanesulfonyl chloride

(2R,4S)-2,5-bis(benzyloxy)-3-methylenepentane-1,4-diol

Downstream raw materials:

(R)-3-benzyloxy-4-(2-benzyloxyethylidene)tetrahydrothiophene

(2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene

(3R,5R)-5-(hydroxymethyl)-4-methylenetetrahydrothiophen-3-ol

(3S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydrothiophen-3-ol