{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

Base Information

Chemical Name:{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester
CAS No.:90497-55-5
Molecular Formula:C₃₀H₃₉N₂O₅PSSi
Molecular Weight:598.775
Hs Code.:

{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

Synonyms:{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

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Chemical Property of {(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

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Technology Process of {(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

There total 6 articles about {(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl 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:

: 19236-58-9
dibenzyl methylphosphonate

: 90497-55-5
{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 1) NaHS, iPr₂NEt / 1) DMF, 0 deg C

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

Reference yield:

: 185446-92-8
(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(methoxycarbonyl)methyl>azetidin-2-one

: 90497-55-5
{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 1) NaHS, iPr₂NEt / 1) DMF, 0 deg C

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

Reference yield:

: 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

: 90497-55-5
{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: DBU / tetrahydrofuran / -15 °C

2: 1) NaHS, iPr₂NEt / 1) DMF, 0 deg C

With sodium hydrogensulfide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)99947-7