(E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

Base Information

Chemical Name:(E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone
CAS No.:127462-55-9
Molecular Formula:C₃₄H₅₄IN₃O₆Si
Molecular Weight:755.809
Hs Code.:

(E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

Synonyms:(E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

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Chemical Property of (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

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Technology Process of (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

There total 43 articles about (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone 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:

: 127462-54-8
(S)-2-((R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-2-{[(S)-2-((E)-(2S,6R,8S)-8-hydroxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-propionic acid

: 127462-55-9
(E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; Yield given. Multistep reaction; 1.) THF, RT, 2.5 h, 2.) benzene, reflux;

Reference yield:

: 1026931-00-9
(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid

: 127462-55-9
(E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

Guidance literature:: With diphenyl phosphoryl azide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 4 ℃; for 72h;
DOI:10.1016/S0040-4039(00)75846-1

Reference yield:

: 42406-77-9
L-tyrosine benzyl ester

: 127462-55-9
(E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

Guidance literature:: Multi-step reaction with 12 steps

1: 91.2 percent / Et₃N / dioxane; H₂O / 24 h / Ambient temperature

2: 93.3 percent / imidazole / dimethylformamide / 7 h / Ambient temperature

3: 82 percent / NaH / dimethylformamide / 3 h

4: 84.9 percent / TFA / CH₂Cl₂ / 4 h / 0 °C

5: 91 percent / Et₃N / CH₂Cl₂ / 10 h / Ambient temperature

6: 86.4 percent / H₂ / 10percent Pd-C / ethanol / 15 h

7: 82.8 percent / N-methylmorpholine, DCC, HOBT / CH₂Cl₂ / 5 h / 0 °C

8: I₂, (AcO)2Hg / acetic acid / 2.5 h / 35 °C

9: 80 percent / 2,6-lutidine, TBSOTf / CH₂Cl₂ / 2.5 h / Ambient temperature

10: 80 percent / HOBT, DCC / tetrahydrofuran / 5 h / 0 °C

11: 1.) ethanedithiol, 2.) trifluoroacetic acid / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) 0 deg C, 4 h

12: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, RT, 2.5 h, 2.) benzene, reflux

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; dmap; ethandithiol; 2,4,6-trichlorobenzoyl chloride; t-butyldimethylsiyl triflate; mercury(II) diacetate; hydrogen; iodine; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;