methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate

Base Information

• Chemical Name: methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate
• CAS No.: 149654-56-8
• Molecular Formula: C₂₅H₃₄O₄Si
• Molecular Weight: 426.628
• Mol file: 149654-56-8.mol

Synonyms:methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate

Chemical Property of methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate

There total 10 articles about methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate 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: 89.0%

methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate (149551-08-6) → methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (149654-56-8)

Guidance literature:

With sodium methylate; In methanol; for 17h; Ambient temperature;

DOI:10.1002/hlca.19930760207

Reference yield:

methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-(formyloxy)cyclopentaneacetate (149551-06-4) → methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (149654-56-8)

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 2.5h; Yield given;

DOI:10.1002/hlca.19930760207

Reference yield:

5-norbornene-2-methanol (13360-81-1,15507-06-9,42070-72-4,42070-82-6,67505-46-8,67671-05-0,67671-06-1,69831-10-3,95-12-5) → methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (149654-56-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

2: 1) (+)-(1R)-α-pinene, BH3-THF, 2) 30percent aq. H2O2, 3N aq. NaOH

3: pyridinium chlorochromate, Celite / CH₂Cl₂ / 4 h / Ambient temperature

4: 3-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 18 h / 4 °C

5: methanol / Heating

6: PPh₃, diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C

7: NH₃ / methanol / 2.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; borane-THF; Celite; ammonia; dihydrogen peroxide; sodium hydrogencarbonate; 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/hlca.19930760207

upstream raw materials:

methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-(formyloxy)cyclopentaneacetate

methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate

5-norbornene-2-methanol

(1R,4R,5S)-5-(<(tert-butyl)diphenylsilyloxy>methyl)bicyclo<2.2.1>heptan-2-one

Downstream raw materials:

[(1R,2S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(6-chloro-purin-9-yl)-cyclopentyl]-acetic acid methyl ester

[(1R,2S,4R)-4-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopentyl]-acetic acid methyl ester

N-{9-[(1R,3S,4R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-hydroxy-ethyl)-cyclopentyl]-9H-purin-6-yl}-benzamide

[(1R,2S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(6-dibenzoylamino-purin-9-yl)-cyclopentyl]-acetic acid methyl ester