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

Base Information

• Chemical Name: (2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene
• CAS No.: 688797-24-2
• Molecular Formula: C₂₀H₂₂O₂S
• Molecular Weight: 326.459
• Mol file: 688797-24-2.mol

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

Chemical Property of (2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene

There total 4 articles about (2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene 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: 50.0%

(4S)-methanesulfonic acid 2-[(1R)-1-benzyloxy-2-(methanesulfonyloxy)ethyl]-1-(benzyloxymethyl)allyl ester (688797-19-5) → (R)-3-benzyloxy-4-(2-benzyloxyethylidene)tetrahydrothiophene (688797-21-9) + (2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene (688797-24-2)

Guidance literature:

With sodium sulfide; In N,N-dimethyl-formamide; at 0 ℃; for 4h;

DOI:10.1021/jo035735b

Reference yield:

methyl 2,5-di-O-benzyl-3-deoxy-3-methylene-D-erythro-pentofuranoside → (2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene (688797-24-2)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / dioxane

2: lithium borohydride / tetrahydrofuran

3: pyridine / CH₂Cl₂

4: 35 percent / sodium sulfide / dimethylformamide / 4 h / 0 °C

With pyridine; hydrogenchloride; sodium sulfide; lithium borohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-200060072

Reference yield:

2,5-di-O-benzyl-3-deoxy-3-methylene-D-erythro-pentofuranose → (2R,4R)-4-benzyloxy-2-(benzyloxymethyl)-3-methylenetetrahydrothiophene (688797-24-2)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium borohydride / tetrahydrofuran

2: pyridine / CH₂Cl₂

3: 35 percent / sodium sulfide / dimethylformamide / 4 h / 0 °C

With pyridine; sodium sulfide; lithium borohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-200060072

upstream raw materials:

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

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

Downstream raw materials:

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

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

9-[(3S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydrothiophen-3-yl]-6-chloro-9H-purine

9-[(3R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydrothiophen-3-yl]-6-chloro-9H-purine