(1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol

Base Information

• Chemical Name: (1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol
• CAS No.: 149796-49-6
• Molecular Formula: C₂₇H₂₈O₄
• Molecular Weight: 416.517
• Mol file: 149796-49-6.mol

Synonyms:(1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol

Chemical Property of (1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol

There total 7 articles about (1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol 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: 45.4%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-t-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol → (1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol (149796-49-6) + (1R,3R,4S)-3-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol (149827-92-9)

Guidance literature:

for 50h; Ambient temperature; Pseudomonas fluorescens lipase;

DOI:10.1002/hlca.19940770608

Reference yield: 43.4%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-t-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol → (1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol (149796-49-6) + (1R,3R,4S)-3-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol (149827-92-9)

Guidance literature:

for 50h; Ambient temperature; Chromobacterium viscosum lipase (CVL);

DOI:10.1016/S0040-4039(00)60482-3

Reference yield:

cis-4-cyclopentene-1,3-diol (29783-26-4) → (1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol (149796-49-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / 2,6-lutidine / CH₂Cl₂ / 0 deg C, 10 min; without cooling, 30 min

2: 95 percent / H₂ / 3)3> / tetrahydrofuran / 5 h / 80 °C / 60004.8 Torr / Au-coated autoclave

3: 98 percent / NaBH₄ / tetrahydrofuran; H₂O / 0.17 h / 0 °C

4: 88 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

5: Bu₄NF*3H₂O / tetrahydrofuran / 5 h / Ambient temperature

6: 43.4 percent / 50 h / Ambient temperature; Pseudomonas fluorescens lipase

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; triethylamine; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/hlca.19940770608

upstream raw materials:

vinyl acetate

cis-4-cyclopentene-1,3-diol

Downstream raw materials:

(1S,3S,4R)-4-<(triphenylmethoxy)methyl>cyclopentane-1,3-diol

(1S,2R,4R)-4-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentan-1-ol