(6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

Base Information

Chemical Name:(6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate
CAS No.:1364706-02-4
Molecular Formula:C₃₁H₄₁IN₄O₈
Molecular Weight:724.593
Hs Code.:

Synonyms:(6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

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Chemical Property of (6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

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Technology Process of (6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

There total 8 articles about (6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate 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: 55.0%

: 15761-38-3
L-N-Boc-Ala

: C₂₃H₂₈IN₃O₅*ClH

: 1364706-02-4
(6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

Guidance literature:: L-N-Boc-Ala; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;

C₂₃H₂₈IN₃O₅*ClH; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo202105v

Reference yield:

: 1364705-71-4
(6S,9S,12S)-methyl 12-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate

: 1364706-02-4
(6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

2.2: 16 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1021/jo202105v

Reference yield:

: 100-39-0
benzyl bromide

: 1364706-02-4
(6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

Guidance literature:: Multi-step reaction with 7 steps

1.1: copper(II) sulfate; sodium hydroxide / water / 0.17 h / 60 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: thionyl chloride / 2 h / 20 °C / Inert atmosphere; Cooling

3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

5.2: 16 h / 0 - 20 °C / Inert atmosphere

6.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere

7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

7.2: 16 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; thionyl chloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; copper(II) sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo202105v