9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine

Base Information

• Chemical Name: 9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine
• CAS No.: 87884-15-9
• Molecular Formula: C₃₂H₃₇N₇O₈
• Molecular Weight: 647.688
• Mol file: 87884-15-9.mol

Synonyms:

Chemical Property of 9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine

There total 7 articles about 9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine 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: 59.0%

1-(6-benzoylamino-purin-9-yl)-6-diethoxyphosphoryl-O2,O3-isopropylidene-1,5,6-trideoxy-heptofuranurononitrile (50466-88-1) + methyl (2S)-2-[(tert-butoxy)carbonylamino]-4-oxobutanoate (87884-14-8) → 9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine (87884-15-9,87935-91-9,99782-54-4)

Guidance literature:

With magnesium hydroxide; In methanol; at 0 ℃;

DOI:10.1021/acschembio.6b00308

Reference yield:

benzoyl chloride (98-88-4) → 9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine (87884-15-9,87935-91-9,99782-54-4)

Guidance literature:

Multi-step reaction with 5 steps

1: chloro-trimethyl-silane; pyridine / 0 °C

2: pyridine / dichloromethane / 0 °C

3: sodium iodide / acetone

4: sodium hydride / dimethyl sulfoxide

5: magnesium hydroxide / methanol / 0 °C

With pyridine; magnesium hydroxide; chloro-trimethyl-silane; sodium hydride; sodium iodide; In methanol; dichloromethane; dimethyl sulfoxide; acetone; 5: |Wittig Olefination;

DOI:10.1021/acschembio.6b00308

Reference yield:

2',3'-isopropylidene adenosine (362-75-4) → 9--6-cyano-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-β-D-ribo-deca-6-enofuranosyluronate>-adenine (87884-15-9,87935-91-9,99782-54-4)

Guidance literature:

Multi-step reaction with 5 steps

1: chloro-trimethyl-silane; pyridine / 0 °C

2: pyridine / dichloromethane / 0 °C

3: sodium iodide / acetone

4: sodium hydride / dimethyl sulfoxide

5: magnesium hydroxide / methanol / 0 °C

With pyridine; magnesium hydroxide; chloro-trimethyl-silane; sodium hydride; sodium iodide; In methanol; dichloromethane; dimethyl sulfoxide; acetone; 5: |Wittig Olefination;

DOI:10.1021/acschembio.6b00308

upstream raw materials:

benzoyl chloride

2',3'-isopropylidene adenosine

N⁶,N⁶-dibenzoyl-5'-deoxy-5'-iodo-2',3'-O-isopropylideneadenosine

N-benzoyl-N-(9-(6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)benzamide

Downstream raw materials:

sinefungin