tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane

Base Information

• Chemical Name: tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane
• CAS No.: 192506-63-1
• Molecular Formula: C₅₆H₆₂O₇Si
• Molecular Weight: 875.19
• Mol file: 192506-63-1.mol

Synonyms:tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane

Chemical Property of tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane

There total 1 articles about tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-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:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + 6-(tert-Butyl-diphenyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol (138695-86-0) → tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane (192506-63-1)

Guidance literature:

With dicobalt octacarbonyl; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; Yield given. Multistep reaction; 1.) Et₂O, room temp., 2.) CH₂Cl₂, 0 deg C, 3.) MeOH, room temp.;

DOI:10.1016/S0040-4039(97)00983-0

Reference yield: 92.0%

tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane (192506-63-1) → 6-Phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-yn-1-ol (192506-64-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(97)00983-0

Reference yield:

tert-Butyl-diphenyl-[6-phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynyloxy]-silane (192506-63-1) → 6-Phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-ynoic acid (3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / TBAF / tetrahydrofuran / Ambient temperature

2: PDC / dimethylformamide / Ambient temperature

3: DCC, DMAP, HOBt, Et₃N / CH₂Cl₂ / Ambient temperature

With dmap; dipyridinium dichromate; tetrabutyl ammonium fluoride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)00983-0

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

6-(tert-Butyl-diphenyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol

Downstream raw materials:

6-Phenyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hex-5-yn-1-ol