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

Base Information

• Chemical Name: methyl (1R,2S,4R)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate
• CAS No.: 802912-08-9
• Molecular Formula: C₂₅H₃₄O₄Si
• Molecular Weight: 426.628
• Mol file: 802912-08-9.mol

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

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

There total 11 articles about methyl (1R,2S,4R)-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: 70.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl (1R,2S,4R)-4-hydroxy-2-(hydroxymethyl)cyclopentaneacetate (802912-07-8) → methyl (1R,2S,4R)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (802912-08-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 40h;

DOI:10.1002/hlca.200490202

Reference yield:

(1R,4R,5S)-5-(hydroxymethyl)bicyclo[2.2.1]heptane-2-one (802912-03-4) → methyl (1R,2S,4R)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (802912-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / NaHCO₃; 3-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 20 °C

2: 90 percent / HCl; water / 20 h / Heating

3: 70 percent / 1H-imidazole / dimethylformamide / 40 h / 20 °C

With 1H-imidazole; hydrogenchloride; water; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Baeyer-Villiger oxidation;

DOI:10.1002/hlca.200490202

Reference yield:

(1R,5R,6S)-6-(hydroxymethyl)-2-oxabicyclo[3.2.1]octan-3-one (802912-06-7) → methyl (1R,2S,4R)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (802912-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / HCl; water / 20 h / Heating

2: 70 percent / 1H-imidazole / dimethylformamide / 40 h / 20 °C

With 1H-imidazole; hydrogenchloride; water; In N,N-dimethyl-formamide;

DOI:10.1002/hlca.200490202

upstream raw materials:

sodium methylate

(1R,5R,6S)-6-(<(tert-butyl)diphenylsilyloxy>methyl)-2-oxabicyclo<3.2.1>octan-3-one

tert-butylchlorodiphenylsilane

methyl (1R,2S,4R)-4-hydroxy-2-(hydroxymethyl)cyclopentaneacetate

Downstream raw materials:

N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-<(tritylthio)methyl>-1'a-carbaadenosine

N⁶-benzoyl-2',3',5'-trideoxy-3'-<(methylsulfonyloxy)methyl>-5'-<(tritylthio)methyl>-1'a-carbaadenosine

N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine

N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-1'a-carbaadenosine