Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester

Base Information

• Chemical Name: Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester
• CAS No.: 743477-85-2
• Molecular Formula: C₂₄H₃₂O₄Si
• Molecular Weight: 412.601
• Mol file: 743477-85-2.mol

Synonyms:Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester

Chemical Property of Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester

There total 5 articles about Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl 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: 89.0%

Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-trityloxymethyl-cyclobutylmethyl ester (743477-84-1) → Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester (743477-85-2)

Guidance literature:

With boron trifluoride diethyl etherate; In methanol; dichloromethane; at 20 ℃;

DOI:10.1021/ol0491989

Reference yield:

1,2-O-cyclohexylidene-trans-cis-2,3-bis(hydroxymethyl)-1-cyclobutanol → Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester (743477-85-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 47.3 percent / Pseudomonas cepacia lipase / 2 h / 28 °C

2: Amberlite 120 IR / methanol / 1 h / 20 °C

3: 3.0 g / pyridine / 20 °C

4: 94.4 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

5: 89 percent / BF₃*OEt₂ / CH₂Cl₂; methanol / 20 °C

With pyridine; 1H-imidazole; Pseudomonas cepacia lipase; Amberlite 120 IR; boron trifluoride diethyl etherate; In methanol; dichloromethane;

DOI:10.1021/ol0491989

Reference yield:

Acetic acid (1S,2S,3S)-3-hydroxy-2-hydroxymethyl-cyclobutylmethyl ester → Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-cyclobutylmethyl ester (743477-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.0 g / pyridine / 20 °C

2: 94.4 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

3: 89 percent / BF₃*OEt₂ / CH₂Cl₂; methanol / 20 °C

With pyridine; 1H-imidazole; boron trifluoride diethyl etherate; In methanol; dichloromethane;

DOI:10.1021/ol0491989

upstream raw materials:

Acetic acid (1S,2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-trityloxymethyl-cyclobutylmethyl ester

C₁₄H₂₂O₄

Acetic acid (1S,2S,3S)-3-hydroxy-2-trityloxymethyl-cyclobutylmethyl ester

Downstream raw materials:

Acetic acid (1S,2R,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-iodomethyl-cyclobutylmethyl ester

Acetic acid (1S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclobutylmethyl ester

(+)-(1S,3S)-3-acetoxymethyl-2-methylene-cyclobutanol