1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone

Base Information

• Chemical Name: 1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone
• CAS No.: 314297-19-3
• Molecular Formula: C₂₇H₃₂F₃NO₅Si
• Molecular Weight: 535.635
• Mol file: 314297-19-3.mol

Synonyms:1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone

Chemical Property of 1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone

There total 5 articles about 1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone 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: 93.0%

trifluoroacetic anhydride (407-25-0) + (2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-hexahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalene (314297-18-2) → 1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone (314297-19-3)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(03)01279-6

Reference yield:

3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose (247025-11-2) → 1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone (314297-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Ph₃P / xylene / Heating

2: 93 percent / DMAP / CH₂Cl₂ / 0 °C

With dmap; triphenylphosphine; In dichloromethane; xylene;

DOI:10.1016/S0040-4039(03)01279-6

Reference yield:

[(3aR,5R,6S,6aR)-6-Amino-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol (314297-15-9) → 1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone (314297-19-3)

Guidance literature:

Multi-step reaction with 4 steps

1: DMAP; Et₃N / CH₂Cl₂ / 20 °C

2: 90 percent / NaH / tetrahydrofuran / 20 °C

3: 66 percent / Na; n-AmOH / 120 - 130 °C

4: 93 percent / DMAP / CH₂Cl₂ / 0 °C

With dmap; pentan-1-ol; sodium; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(03)01279-6

upstream raw materials:

trifluoroacetic anhydride

(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-hexahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalene

3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose

[(3aR,5R,6S,6aR)-6-Amino-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

Downstream raw materials:

Acetic acid (1S,3R,4R,5S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester

Acetic acid (1S,4R,5S)-3-acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester