(+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane

Base Information

• Chemical Name: (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane
• CAS No.: 324015-67-0
• Molecular Formula: C₂₂H₂₈O₄SSi
• Molecular Weight: 416.613
• Mol file: 324015-67-0.mol

Synonyms:(+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane

Chemical Property of (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane

There total 6 articles about (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane 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:

(+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane (139757-71-4) → (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane (324015-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Pb(OAc)4 / ethyl acetate / 0.17 h / Ambient temperature

2: pyridinium dichromate (PDC) / dimethylformamide / 8 h / Ambient temperature

3: pyridine / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; lead(IV) acetate; dipyridinium dichromate; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00054a001

Reference yield:

tert-Butyl-[(2R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane (1025959-81-2) → (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane (324015-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1: p-TsOH*H₂O / methanol / 0.5 h / Ambient temperature

2: Pb(OAc)4 / ethyl acetate / 0.17 h / Ambient temperature

3: pyridinium dichromate (PDC) / dimethylformamide / 8 h / Ambient temperature

4: pyridine / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; lead(IV) acetate; dipyridinium dichromate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00054a001

Reference yield:

lead(IV) tetraacetate (546-67-8) + (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carboxylic acid (139689-04-6) → (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane (324015-67-0)

Guidance literature:

With pyridine; In tetrahydrofuran; for 0.5h; Yield given; Ambient temperature;

DOI:10.1021/jm00054a001

upstream raw materials:

lead(IV) tetraacetate

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carboxylic acid

(+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane

tert-Butyl-[(2R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane

Downstream raw materials:

(+)-(2R,5S)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine

(+)-(2R,5R)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine

(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine

(2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine