(-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol

Base Information

• Chemical Name: (-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol
• CAS No.: 881915-53-3
• Molecular Formula: C₂₁H₂₈O₂SSi
• Molecular Weight: 372.604
• Mol file: 881915-53-3.mol

Synonyms:(-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol

Chemical Property of (-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol

There total 5 articles about (-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol 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:

(2R,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-thietane-3-carbaldehyde → (-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol (881915-53-3)

Guidance literature:

(2R,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-thietane-3-carbaldehyde; With sodium methylate; In methanol; for 16h;

With sodium tetrahydroborate; In methanol; for 2h;

DOI:10.1021/jm050912h

Reference yield:

(-)-(2R)-tert-butyl-(3-methylene-thietan-2-ylmethoxy)-diphenylsilane (881915-51-1) → (-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol (881915-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 2.5 h / 0 - 20 °C

1.2: 64 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2 h

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: NaOMe / methanol / 16 h

3.2: NaBH₄ / methanol / 2 h

With oxalyl dichloride; dimethylsulfide borane complex; sodium methylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation;

DOI:10.1021/jm050912h

Reference yield:

(-)-(2S,3S)-2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-ol (881915-50-0) → (-)-(2R,3R)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol (881915-53-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Ac₂O; DMSO / 20 °C

2.1: titanocene dichloride / tetrahydrofuran; diethyl ether / 2 h / 20 °C

2.2: 4.12 g / diethyl ether; tetrahydrofuran / 48 h / Heating

3.1: BH₃*SMe₂ / tetrahydrofuran / 2.5 h / 0 - 20 °C

3.2: 64 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2 h

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: NaOMe / methanol / 16 h

5.2: NaBH₄ / methanol / 2 h

With oxalyl dichloride; dimethylsulfide borane complex; titanocene dichloride; sodium methylate; acetic anhydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Moffatt oxidation / 4.1: Swern oxidation;

DOI:10.1021/jm050912h

upstream raw materials:

(-)-(2R)-tert-butyl-(3-methylene-thietan-2-ylmethoxy)-diphenylsilane

(-)-(2S,3S)-2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-ol

(-)-(2R,3S)-[2-(tert-butyldiphenylsilanyloxymethyl)thietan-3-yl]methanol

Downstream raw materials:

(-)-(2R,3R)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietane

1-[(2R,3S,4R/S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]cytosine

9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloropurine

9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]hypoxanthine