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

Base Information

• Chemical Name: (+)-(2R,5S)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine
• CAS No.: 145913-73-1
• Molecular Formula: C₂₅H₂₇ClN₄O₂SSi
• Molecular Weight: 511.119
• Mol file: 145913-73-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (+)-(2R,5S)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 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: 35.0%

(+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane (324015-67-0) + 6-chloropurine (87-42-3) → (+)-(2R,5S)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine (145913-73-1) + (+)-(2R,5R)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine (145986-33-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1.) RT, 30 min, 2.) reflux, 14 h;

DOI:10.1021/jm00054a001

Reference yield: 30.1%

6-chloro-9-trimethylsilylpurine (32865-86-4) + (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane (324015-67-0) → (+)-(2R,5S)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine (145913-73-1) + (+)-(2R,5R)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine (145986-33-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1.) RT, 30 min, 2.) reflux, 14 h;

DOI:10.1021/jm00054a001

Reference yield:

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde (148774-90-7) → (+)-(2R,5S)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine (145913-73-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine / tetrahydrofuran / 0.5 h / Ambient temperature

3: 35 percent / trimethylsilyl triflate (TMSOTf) / CH₂Cl₂ / 1.) RT, 30 min, 2.) reflux, 14 h

With pyridine; dipyridinium dichromate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00054a001

upstream raw materials:

6-chloro-9-trimethylsilylpurine

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

6-chloropurine

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

Downstream raw materials:

(+)-(2R,5S)-6-chloro-9-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>purine

(+)-(2R,5S)-9-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>adenine

(+)-(2R,5S)-N⁶-methyl-9-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>adenine