[3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester

Base Information

• Chemical Name: [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester
• CAS No.: 428499-81-4
• Molecular Formula: C₃₃H₄₁N₆O₆PS
• Molecular Weight: 680.765
• Mol file: 428499-81-4.mol

Synonyms:

Chemical Property of [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester

There total 3 articles about [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl 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: 63.0%

5'-acetylthio-5'-deoxy-2',3'-O-isopropylidene adenosine (84365-04-8) + [1-(benzhydrylidene-amino)-3-bromo-propyl]-phosphonic acid diethyl ester (428499-80-3) → [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester (428499-81-4)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1016/S0960-894X(01)00789-2

Reference yield:

diethyl N-(diphenylmethylene) aminomethyl phosphonate (122570-91-6) → [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester (428499-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / n-BuLi / tetrahydrofuran / -78 °C

2: 63 percent / KOH / methanol

With potassium hydroxide; n-butyllithium; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(01)00789-2

Reference yield:

diethyl 1-(diphenylmethylamino)methylphosphonate (80993-30-2) → [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester (428499-81-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / DDQ; 4A molecular sieves / benzene

2: 38 percent / n-BuLi / tetrahydrofuran / -78 °C

3: 63 percent / KOH / methanol

With potassium hydroxide; n-butyllithium; 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; benzene;

DOI:10.1016/S0960-894X(01)00789-2

upstream raw materials:

5'-acetylthio-5'-deoxy-2',3'-O-isopropylidene adenosine

[1-(benzhydrylidene-amino)-3-bromo-propyl]-phosphonic acid diethyl ester

diethyl N-(diphenylmethylene) aminomethyl phosphonate

diethyl 1-(diphenylmethylamino)methylphosphonate