Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

Base Information

Chemical Name:Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester
CAS No.:90510-08-0
Molecular Formula:C₂₉H₃₇F₃NO₈PSSi
Molecular Weight:675.735
Hs Code.:

Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

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Chemical Property of Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

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Technology Process of Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

There total 6 articles about Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl 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:

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 86530-03-2,90581-07-0
{(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,7-dioxo-1-aza-bicyclo[3.2.0]hept-2-yl}-phosphonic acid dibenzyl ester

: 90510-08-0
Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at -15 ℃;
DOI:10.1016/S0040-4039(00)99947-7

Reference yield:

: 358-23-6
trifluoromethylsulfonic anhydride

: 86530-03-2,90581-07-0
{(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,7-dioxo-1-aza-bicyclo[3.2.0]hept-2-yl}-phosphonic acid dibenzyl ester

: 90510-08-0
Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)99947-7

Reference yield:

: 19236-58-9
dibenzyl methylphosphonate

: 90510-08-0
Trifluoro-methanesulfonic acid (5R,6S)-2-(bis-benzyloxy-phosphoryl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1) nBuLi / 1) THF, -78 deg C

2: 71 percent / 1,8-diazabicyclo(5.4.0)undec-7-ene, p-dodecylbenzenesulfonylazide / CH₂Cl₂

3: 74 percent / Rh₂(OAc)4 / CH₂Cl₂ / Heating

4: DBU / tetrahydrofuran / -15 °C

With dirhodium tetraacetate; n-butyllithium; 4-dodecylbenzenesulphonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(00)99947-7