9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine

Base Information

• Chemical Name: 9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine
• CAS No.: 85681-08-9
• Molecular Formula: C₃₃H₄₁N₅O₆Si
• Molecular Weight: 631.804
• Mol file: 85681-08-9.mol

Synonyms:

Chemical Property of 9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine

There total 6 articles about 9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>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: 90.0%

9--2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronate>adenine (85681-06-7,85701-31-1) → 9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine (85681-08-9,85681-09-0,126721-34-4)

Guidance literature:

With sodium hydroxide; water; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo00160a008

Reference yield:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) → 9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine (85681-08-9,85681-09-0,126721-34-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / benzene; acetonitrile; CH₂Cl₂ / 1 h / 60 °C

2: 90 percent / H₂ / PtO₂ / ethanol / 50 h / 3102.9 Torr

3: 77 percent / ethane-1,2-diol / 6 h / 110 °C

4: NaOH / ethanol; H₂O / 1 h / 80 °C

5: imidazole / dimethylformamide / 5 h / Ambient temperature

6: 90 percent / NaOH, H₂O / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; sodium hydroxide; water; hydrogen; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo00160a008

Reference yield:

(E)-N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-5'-deoxyadenosine (85681-03-4) → 9-<6-(R,S)-<2-(tert-butyldiphenylsiloxy)ethyl>-2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronic acid>adenine (85681-08-9,85681-09-0,126721-34-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / H₂ / PtO₂ / ethanol / 50 h / 3102.9 Torr

2: 77 percent / ethane-1,2-diol / 6 h / 110 °C

3: NaOH / ethanol; H₂O / 1 h / 80 °C

4: imidazole / dimethylformamide / 5 h / Ambient temperature

5: 90 percent / NaOH, H₂O / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; sodium hydroxide; water; hydrogen; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; ethylene glycol; N,N-dimethyl-formamide;

DOI:10.1021/jo00160a008

upstream raw materials:

9--2,3-O-isopropylidene-5,6-dideoxy-β-D-ribo-heptofuranosyluronate>adenine

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde

N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

2',3'-O-Isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

Downstream raw materials:

{(S)-1-[(3aS,4S,6S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-3-hydroxy-propyl}-carbamic acid benzyl ester

Methanesulfonic acid (S)-4-[(3aS,4S,6S,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-benzyloxycarbonylamino-butyl ester

[(S)-1-[(3aS,4S,6S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-carbamic acid benzyl ester

2-{(S)-4-[(3aS,4S,6S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-benzyloxycarbonylamino-butyl}-malonic acid dibenzyl ester