(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Base Information

Chemical Name:(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester
CAS No.:156706-65-9
Molecular Formula:C₄₇H₇₂IN₃O₁₀Si
Molecular Weight:994.093
Hs Code.:

(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Synonyms:(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

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Chemical Property of (E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

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Technology Process of (E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

There total 18 articles about (E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl 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: 84.0%

: 156706-63-7
(S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionic acid

: 156767-16-7
(E)-(2S,6R,8R)-8-Hydroxy-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

: 156706-65-9
(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 16h; Ambient temperature;
DOI:10.1016/S0040-4039(00)75846-1

Reference yield:

: 117289-84-6
(E)-(2S,6R,8S)-8-{[tert-butyl(dimethyl)silyl]oxy}-2,4,6-trimethylnon-4-enoic acid

: 156706-65-9
(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / DCC, DMAP / CH₂Cl₂ / 0 deg C, 1 h; RT, 24 h

2: 84 percent / TBAF / tetrahydrofuran / 16 h / Ambient temperature

3: 1) PPh₃, DEAD, HCOOH, 2) MeOH, aq. NaHCO₃ / 1) Et₂O, 0 deg C 10 min then RT, 1 h

4: 84 percent / PPh₃, DEAD / tetrahydrofuran / 0 deg C, 30 min; RT, 16 h

With methanol; dmap; formic acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.3987/COM-97-S41

Reference yield:

: 119706-75-1
(R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid

: 156706-65-9
(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1) 1,7 M Bu^tLi in pentane / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C to RT, 7.5 h

2: 79 percent / diethyl phosphonocyanide, Et₃N / dimethylformamide / 0 deg C, 30 min; RT, 16 h

3: TMSOTf / CH₂Cl₂ / 1.5 h / 0 °C

4: bis(2-oxo-3-oxazolidinyl)phosphonic chloride, Et₃N / CH₂Cl₂ / 72 h / 4 °C

5: 99 percent / I₂, Hg(OAc)2 / acetic acid / 24 h / 45 °C

6: 95 percent / 1 N NH₄OAc in H₂O, Zn / tetrahydrofuran / 18 h / Ambient temperature

7: 84 percent / PPh₃, DEAD / tetrahydrofuran / 0 deg C, 30 min; RT, 16 h

With diethyl cyanophosphonate; trimethylsilyl trifluoromethanesulfonate; mercury(II) diacetate; ammonium acetate; iodine; tert.-butyl lithium; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.3987/COM-97-S41