(2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol
CAS No.:183170-29-8
Molecular Formula:C₃₀H₃₆O₈
Molecular Weight:524.611
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

There total 6 articles about (2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol 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: 48.0%

: methyl 2-O-benzyl-3-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside

: 162583-79-1
methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-glucopyranoside

: 183170-29-8
(2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 3.5h; Ambient temperature;
DOI:10.1021/jo961158y

Reference yield:

: 18929-63-0
methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

: 183170-29-8
(2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

2: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

3: 28 percent / trimethylsilyl chloride, sodium cyanoborohydride / acetonitrile / 3.5 h / Ambient temperature

With chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo961158y

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 183170-29-8
(2R,3R,4S,5R,6S)-5-Benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 70 °C

2: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

3: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

4: 28 percent / trimethylsilyl chloride, sodium cyanoborohydride / acetonitrile / 3.5 h / Ambient temperature

With chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo961158y