(2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol
CAS No.:210755-77-4
Molecular Formula:C₃₀H₅₂O₁₀Si
Molecular Weight:600.822
Hs Code.:

(2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

Synonyms:(2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

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Chemical Property of (2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

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Technology Process of (2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

There total 10 articles about (2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 210755-76-3
methyl 4-C-(6-O-benzyl-3-O-methyl-α-D-glucopyranosylmethyl)-4-deoxy-2,3-di-O-methyl-α-D-glucopyranoside

: 210755-77-4
(2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1016/S0960-894X(97)00252-7

Reference yield:

: methyl 4-C-(4,6-O-benzylidene-3-O-methyl-α-D-glucopyranosylmethyl)-4-deoxy-2,3-di-O-methyl-α-D-glucopyranoside

: 210755-77-4
(2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1: DMAP / pyridine

2: 87 percent / HCl, NaBH₃CN, 4 Angstroem molecular sieves / tetrahydrofuran; diethyl ether / 1.5 h

3: 98 percent / sodium / methanol / 0.5 h / Ambient temperature

4: 86 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; dmap; 4 A molecular sieve; sodium; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane;

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 210755-77-4
(2R,3R,4R,5S,6R)-2-Benzyloxymethyl-6-[(2S,3R,4S,5R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran-3-ylmethyl]-4-methoxy-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / APTS / acetonitrile / Ambient temperature

2: 1.) BuLi, 2.) imidazole / 1.) THF, 2.) THF

3: 1.) Bu₃SnH, AIBN, 2.) 40percent aq. HF / 1.) toluene, 2.) THF

5: 86 percent / Et₃N, DMAP / CH₂Cl₂

With 1H-imidazole; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; triethylamine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; In dichloromethane; acetonitrile;
DOI:10.1016/S0960-894X(97)00252-7