{2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: {2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane
• CAS No.: 165545-46-0
• Molecular Formula: C₃₂H₃₉Br₂ClO₃Si
• Molecular Weight: 695.006
• Mol file: 165545-46-0.mol

Synonyms:{2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

Chemical Property of {2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

There total 1 articles about {2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane 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: 64.0%

2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine (165545-45-9) → {2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane (165545-46-0)

Guidance literature:

With tert.-butylnitrite; copper(ll) bromide; Ambient temperature;

DOI:10.1021/ja00135a021

Reference yield: 93.0%

{2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane (165545-46-0) → (2R,3R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-2-(2,2-dibromo-ethyl)-tetrahydro-pyran-3-ol (165545-47-1)

Guidance literature:

With boron trichloride;

DOI:10.1021/ja00135a021

Reference yield:

{2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane (165545-46-0) → [2-((2S,3S,4aR,6S,7R,8aR)-7-Bromo-3-chloro-6-ethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane (165545-50-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / BCl₃

2: 95 percent / NMM

3: 75 percent / Bu₃SnH, AIBN / benzene / Heating

4: LiAlH₄

5: I₂, Ph₃P, imidazole

6: 89 percent / LiEt₃BH

With 4-methyl-morpholine; 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; boron trichloride; lithium triethylborohydride; triphenylphosphine; In benzene;

DOI:10.1021/ja00135a021

upstream raw materials:

2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine

Downstream raw materials:

(2R,3R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-2-(2,2-dibromo-ethyl)-tetrahydro-pyran-3-ol

[2-((2S,3S,4aR,6S,7R,8aR)-7-Bromo-3-chloro-6-ethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

{(2S,3R,4aR,6S,7S,8aR)-3-Bromo-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-7-chloro-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester

(E)-3-[(2R,3R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-2-(2,2-dibromo-ethyl)-tetrahydro-pyran-3-yloxy]-acrylic acid methyl ester