(9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester

Base Information

• Chemical Name: (9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester
• CAS No.: 102423-06-3
• Molecular Formula: C₃₄H₃₃N₅O₆
• Molecular Weight: 607.666
• Mol file: 102423-06-3.mol

Synonyms:(9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester

Chemical Property of (9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester

There total 5 articles about (9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester 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: 97.0%

5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine (102423-04-1) → (9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester (102423-06-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo00362a052

Reference yield:

Carbonic acid allyl ester (2R,3S,5R)-2-hydroxymethyl-5-[4-(4-methoxy-benzoylamino)-2-oxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester → (9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester (102423-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / t-BuLi / tetrahydrofuran / 0.08 h / -78 °C

2: 97 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran

With tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran;

DOI:10.1021/jo00362a052

Reference yield:

N-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2,3,4-tetrahydro-pyrimidin-4-yl)-4-methoxy-benzamide → (9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester (102423-06-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / t-BuMgCl

2: dichloroacetic acid

3: 95 percent / t-BuLi / tetrahydrofuran / 0.08 h / -78 °C

4: 97 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran

With dichloro-acetic acid; tert-butylmagnesium chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran;

DOI:10.1021/jo00362a052

upstream raw materials:

5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine

9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine

Downstream raw materials:

9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine

5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine

2'-deoxy-5-O-[(4-methoxyphenyl)(diphenyl)methyl]adenosine