2-Oxa-6-azabicyclo[3.2.0]heptane-3,4-diol, 1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-6-(trifluoroacetyl)-, diacetate (ester), (1S,4R,5S)-

Base Information

• Chemical Name: 2-Oxa-6-azabicyclo[3.2.0]heptane-3,4-diol, 1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-6-(trifluoroacetyl)-, diacetate (ester), (1S,4R,5S)-
• CAS No.: 314297-21-7
• Molecular Formula: C28H32F3NO7Si
• Molecular Weight: 579.645
• Mol file: 314297-21-7.mol

Synonyms:

Chemical Property of 2-Oxa-6-azabicyclo[3.2.0]heptane-3,4-diol, 1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-6-(trifluoroacetyl)-, diacetate (ester), (1S,4R,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxa-6-azabicyclo[3.2.0]heptane-3,4-diol, 1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-6-(trifluoroacetyl)-, diacetate (ester), (1S,4R,5S)-

There total 5 articles about 2-Oxa-6-azabicyclo[3.2.0]heptane-3,4-diol, 1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-6-(trifluoroacetyl)-, diacetate (ester), (1S,4R,5S)- 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: 82.0%

acetic anhydride (108-24-7) + 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) → 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 (314297-21-7)

Guidance literature:

In sulfuric acid; acetic acid; at 20 ℃;

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) → 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 (314297-21-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / Ph₃P / xylene / Heating

2: 93 percent / DMAP / CH₂Cl₂ / 0 °C

3: 82 percent / acetic acid; H₂SO₄ / 20 °C

With dmap; triphenylphosphine; In dichloromethane; sulfuric acid; acetic acid; xylene;

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

Reference yield:

(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) → 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 (314297-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / DMAP / CH₂Cl₂ / 0 °C

2: 82 percent / acetic acid; H₂SO₄ / 20 °C

With dmap; In dichloromethane; sulfuric acid; acetic acid;

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

upstream raw materials:

acetic anhydride

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

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

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

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