(2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol

Base Information

• Chemical Name: (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol
• CAS No.: 221459-89-8
• Molecular Formula: C₁₁H₂₄O₃Si
• Molecular Weight: 232.395

Synonyms:(2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol

Chemical Property of (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol

Chemical Property:

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Technology Process of (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol

There total 1 articles about (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol (221459-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / imidazole / CH₂Cl₂

2: DIBAL-H / CH₂Cl₂

With 1H-imidazole; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1055/s-2007-983781

Reference yield: 47.0%

3,5-di-tert-butyl-4-methoxybenzenethiol + (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol (221459-89-8) → 1-(3',5'-di-tert-butyl-4'-methoxyphenylsulfanyl)-5-O-(tert-butyldimethylsilyl)-α-D-glycero-pentofuranoside (868700-21-4) + 1-(3',5'-di-tert-butyl-4'-methoxyphenylsulfanyl)-5-O-(tert-butyldimethylsilyl)-β-D-glycero-pentofuranoside

Guidance literature:

With montmorillonite K-10; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol051776d

Reference yield: 26.0%

4-diphenylamino-benzenethiol + (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol (221459-89-8) → 1-[4'-(N,N-diphenylamino)phenylsulfanyl]-5-O-(tert-butyldimethylsilyl)-α-D-glycero-pentofuranoside + 1-[4'-(N,N-diphenylamino)phenylsulfanyl]-5-O-(tert-butyldimethylsilyl)-β-D-glycero-pentofuranoside

Guidance literature:

With montmorillonite K-10; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1021/ol051776d

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

1-(3',5'-di-tert-butyl-4'-methoxyphenylsulfanyl)-5-O-(tert-butyldimethylsilyl)-α-D-glycero-pentofuranoside

(4E,10E)-(8S,9S,12S,13R,14S,16R)-20-Benzyloxy-9-hydroxy-8,14,19-trimethoxy-13-methoxymethoxy-4,10,12,16-tetramethyl-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,10,18,20-pentaen-3-one

(2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-hydroxy-11-(methoxymethoxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,8-dienoate

(4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid 20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester

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