[(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

Base Information

• Chemical Name: [(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol
• CAS No.: 163854-66-8
• Molecular Formula: C₃₄H₄₆O₆Si
• Molecular Weight: 578.821

Synonyms:[(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

Chemical Property of [(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

Chemical Property:

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Technology Process of [(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

There total 1 articles about [(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol 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%

(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-2H-pyran-2-carboxylate (177213-24-0) → [(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol (163854-66-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/0040-4039(95)00121-R

Reference yield: 95.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + [(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol (163854-66-8) → Diisopropyl-phosphoramidous acid 2-cyano-ethyl ester (2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-ylmethyl ester (163959-17-9,163854-67-9,183071-96-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 0.0833333h;

DOI:10.1016/0040-4039(95)00121-R

Reference yield:

[(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methanol (163854-66-8) + 2-naphthaloyl chloride (2243-83-6) → Naphthalene-2-carboxylic acid (2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

With pyridine; dmap; at 25 ℃; for 0.75h;

DOI:10.1016/0040-4039(95)00121-R

upstream raw materials:

(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-2H-pyran-2-carboxylate

Downstream raw materials:

Diisopropyl-phosphoramidous acid 2-cyano-ethyl ester (2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-ylmethyl ester

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