N₁,N₆-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide

Base Information

• Chemical Name: N₁,N₆-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide
• CAS No.: 890653-19-7
• Molecular Formula: C₅₀H₆₆I₂N₂O₈Si₂
• Molecular Weight: 1133.06

Synonyms:N₁,N₆-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide

Chemical Property of N₁,N₆-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide

Chemical Property:

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Technology Process of N₁,N₆-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide

There total 1 articles about N₁,N₆-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide 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: 77.0%

N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-(2R,3R,4R,5R)-2,5-bis(2-iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide (890653-17-5) + tert-butyldimethylsilyl chloride (18162-48-6) → N1,N6-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide (890653-19-7) + (2R,3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-2,5-bis-(2-iodo-benzyloxy)-hexanedioic acid bis-{[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-amide}

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2005.11.093

Reference yield: 66.0%

N1,N6-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide (890653-19-7) → N1,N6-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(2-carbamoylbenzyloxy)-3,4-dihydroxyhexane-1,6-diamine (890653-21-1)

Guidance literature:

With hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 120 ℃; for 0.333333h; microwave irradiation;

DOI:10.1016/j.tet.2005.11.093

Reference yield:

N1,N6-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide (890653-19-7) → N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-(2R,3R,4R,5R)-2,5-bis(2-carbamoyl-benzyloxy)-3,4-dihydroxyhexane-1,6-diamine

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / hydroxylamine hydrochloride; ethyldiisopropylamine; DBU / Herrmann's palladacycle; [(t-Bu)3PH]BF₄ / dioxane / 0.33 h / 120 °C / microwave irradiation

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/j.tet.2005.11.093

upstream raw materials:

N₁,N₆-bis[(1S,2R)-2-hydroxy-1-indanyl]-(2R,3R,4R,5R)-2,5-bis(2-iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide

tert-butyldimethylsilyl chloride

Downstream raw materials:

N₁,N₆-bis[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-(2R,3R,4R,5R)-2,5-bis(2-carbamoylbenzyloxy)-3,4-dihydroxyhexane-1,6-diamine

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