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

Base Information

• Chemical Name: 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
• CAS No.: 890653-21-1
• Molecular Formula: C₅₂H₇₀N₄O₁₀Si₂
• Molecular Weight: 967.32

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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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(2-carbamoylbenzyloxy)-3,4-dihydroxyhexane-1,6-diamine

There total 3 articles about 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 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: 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-hydroxy-1-indanyl]-(2R,3R,4R,5R)-2,5-bis(2-iodobenzyloxy)-3,4-dihydroxyhexane-1,6-diamide (890653-17-5) → 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:

Multi-step reaction with 2 steps

1: 77 percent / DMAP / dimethylformamide / 18 h / 20 °C

2: 66 percent / hydroxylamine hydrochloride; ethyldiisopropylamine; DBU / Herrmann's palladacycle; [(t-Bu)3PH]BF₄ / dioxane / 0.33 h / 120 °C / microwave irradiation

With dmap; 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; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.11.093

Reference yield:

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(2-carbamoylbenzyloxy)-3,4-dihydroxyhexane-1,6-diamine (890653-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / DMAP / dimethylformamide / 18 h / 20 °C

2: 66 percent / hydroxylamine hydrochloride; ethyldiisopropylamine; DBU / Herrmann's palladacycle; [(t-Bu)3PH]BF₄ / dioxane / 0.33 h / 120 °C / microwave irradiation

With dmap; 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; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.11.093

upstream raw materials:

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

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

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