5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine

Base Information

• Chemical Name: 5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine
• CAS No.: 149654-60-4
• Molecular Formula: C₃₈H₄₃N₅O₃SSi
• Molecular Weight: 677.943
• Mol file: 149654-60-4.mol

Synonyms:5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine

Chemical Property of 5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine

There total 17 articles about 5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine 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:

methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (149654-56-8) → 5'-<(acetylthio)methyl>-N6-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine (149654-60-4)

Guidance literature:

DOI:10.1002/hlca.19930760207

Reference yield:

benzoyl chloride (98-88-4) → 5'-<(acetylthio)methyl>-N6-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine (149654-60-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: lithium triethylborohydride / tetrahydrofuran / -18 °C

3: PPh₃, diethylazodicarboxylate

With pyridine; lithium triethylborohydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1016/0040-4039(91)85031-Y

Reference yield:

[(1R,2S,4R)-4-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopentyl]-acetic acid methyl ester (138903-97-6,148553-42-8) → 5'-<(acetylthio)methyl>-N6-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine (149654-60-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: lithium triethylborohydride / tetrahydrofuran / -18 °C

3: PPh₃, diethylazodicarboxylate

With pyridine; lithium triethylborohydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1016/0040-4039(91)85031-Y

upstream raw materials:

methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate

N-{9-[(1R,3S,4R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-hydroxy-ethyl)-cyclopentyl]-9H-purin-6-yl}-benzamide

tiolacetic acid

5-norbornene-2-methanol

Downstream raw materials:

N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-1'a-carbaadenosine

N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-<(tritylthio)methyl>-1'a-carbaadenosine

N⁶-benzoyl-2',3',5'-trideoxy-3'-<(methylsulfonyloxy)methyl>-5'-<(tritylthio)methyl>-1'a-carbaadenosine

N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine