Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester

Base Information

• Chemical Name: Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester
• CAS No.: 126798-09-2
• Molecular Formula: C₂₃H₂₆O₇S
• Molecular Weight: 446.521
• Mol file: 126798-09-2.mol

Synonyms:Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester

Chemical Property of Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester

There total 3 articles about Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl 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:

(3aS,4S,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (89291-76-9,126874-34-8) → Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester (126798-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaH / 1) DMF, 40 min, 2) DMF, r.t., 40 min

2: 82 percent / 40percent trifluoroacetic acid / 0.42 h / Ambient temperature

With sodium hydride; trifluoroacetic acid;

DOI:10.1021/jo00033a031

Reference yield:

acetic anhydride (108-24-7) + (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-2-cyclopentene-4,5-diol (126798-05-8) + methanesulfonyl chloride (124-63-0) → (1α,4β,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-azido-5-(acetyloxy)-2-cyclopentene + Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester (126798-09-2)

Guidance literature:

With dmap; lithium azide; triethylamine; Multistep reaction; 1.) CH₂Cl₂, rt, 30 min; 2.) CH₂Cl₂, rt, 30 min; 3.) DMSO, rt, 30 min;

DOI:10.1016/S0040-4039(01)80539-6

Reference yield:

acetic anhydride (108-24-7) + (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-2-cyclopentene-4,5-diol (126798-05-8) → (1α,4β,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-azido-5-(acetyloxy)-2-cyclopentene + Acetic acid (1S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxy-cyclopent-2-enyl ester (126798-09-2)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00033a031

upstream raw materials:

acetic anhydride

(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-2-cyclopentene-4,5-diol

methanesulfonyl chloride

(3aS,4S,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Downstream raw materials:

(1β,2α,5α)-1-N-(5-amino-6-chloropyrimidin-4-yl)-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopentenylamine

9-<(1β,2α,5α)-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopenten-1-yl>-6-chloropurine

(1β,2α,5α)-1-amino-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopentene

(+/-)-neplanocin F