(1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane

Base Information

• Chemical Name: (1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane
• CAS No.: 212911-10-9
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439
• Mol file: 212911-10-9.mol

Synonyms:(1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane

Chemical Property of (1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane

There total 1 articles about (1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane 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: 93.4%

benzoyl chloride (98-88-4) + (1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol (192118-38-0) → (1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane (212911-10-9)

Guidance literature:

With pyridine; for 12h; Ambient temperature;

DOI:10.1016/S0960-894X(98)00278-9

Reference yield:

(1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane (212911-10-9) → (1S,4R)-1-benzyloxy-4-(tert-butoxymethyl)cyclopent-2-ene (212911-13-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.3 percent / conc. HCl / methanol / 2.5 h / 20 °C

2: pyridinium p-toluene-sulfonate / 2 h / 20 °C

3: Ac₂O / 6 h / 120 - 130 °C

With hydrogenchloride; pyridinium p-toluenesulfonate; acetic anhydride; In methanol; 1: Hydrolysis / 2: ortho esterification / 3: Elimination;

DOI:10.1021/jm9901327

Reference yield:

(1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane (212911-10-9) → (1aS,3aS,4R,6S)-4-benzoyloxy-(6-tert-butoxymethyl)-3a,4,5,6,6a-tetrahydrocyclopenta-1,3-dioxole-2-thione (241806-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 93.3 percent / conc. HCl / methanol / 2.5 h / 20 °C

2: 78 percent / acetonitrile / 24 h / 20 °C

With hydrogenchloride; In methanol; acetonitrile; 1: Hydrolysis / 2: thiocarbonylation;

DOI:10.1021/jm9901327

upstream raw materials:

benzoyl chloride

(1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol

Downstream raw materials:

(1S,4R)-1-benzyloxy-4-(tert-butoxymethyl)cyclopent-2-ene

[(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol

(1aS,3aS,4R,6S)-4-benzoyloxy-(6-tert-butoxymethyl)-3a,4,5,6,6a-tetrahydrocyclopenta-1,3-dioxole-2-thione