N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide

Base Information

• Chemical Name: N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide
• CAS No.: 214139-79-4
• Molecular Formula: C₅₀H₆₈N₂O₈Si₂
• Molecular Weight: 881.27

Synonyms:N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide

Chemical Property of N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide

Chemical Property:

Purity/Quality:

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Technology Process of N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide

There total 1 articles about N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide 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: 57.0%

t-butyldimethylsiyl triflate (69739-34-0) + BEA369 (213895-65-9) → (2R,3R,4R,5R)-2,5-Bis-benzyloxy-3,4-dihydroxy-hexanedioic acid [(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-amide ((1S,2R)-2-hydroxy-indan-1-yl)-amide + N1,N6-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide (214139-79-4)

Guidance literature:

With lutidine; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1016/S0040-4020(00)00220-9

Reference yield: 92.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + N1,N6-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide (214139-79-4) → N1,N6-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxy-3,4-O-thiocarbonylhexanediamide (214139-80-7)

Guidance literature:

In 1,2-dichloro-ethane; for 22h; Heating;

DOI:10.1016/S0040-4020(00)00220-9

Reference yield:

N1,N6-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxyhexanediamide (214139-79-4) → BEA425

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 1,2-dichloro-ethane / 22 h / Heating

2: 20 percent / Bu₃SnH; AIBN / toluene / 20 h / Heating

3: 34 percent / H⁺-Dowex / methanol / 72 h / 20 °C

With 2,2'-azobis(isobutyronitrile); H⁺-Dowex; tri-n-butyl-tin hydride; In methanol; 1,2-dichloro-ethane; toluene; 1: Substitution / 2: Reduction / 3: desilylation;

DOI:10.1016/S0040-4020(00)00220-9

upstream raw materials:

t-butyldimethylsiyl triflate

BEA369

Downstream raw materials:

N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R,4R-dihydroxy-3,4-O-thiocarbonylhexanediamide

N₁,N₆-di(2R-t-butyldimethylsilyloxy-1S-indanyl)-2R,5R-dibenzyloxy-3R-hydroxyhexanediamide

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