(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester
CAS No.:1054630-28-2
Molecular Formula:C₃₀H₄₅NO₁₅
Molecular Weight:659.685
Hs Code.:

(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Synonyms:(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

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Chemical Property of (2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

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Technology Process of (2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

There total 12 articles about (2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester 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:

: 87905-98-4
5-<(benzyloxycarbonyl)amino>pentanol

: 1054630-28-2
(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / 2,4,6-trimethylpyridine, AgOTf, 3-Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / 0 °C

2: 1) TMSOTf, 2) pyridine / 1) CH₂Cl₂, -20 deg C, 1 h, 2) RT, 16 h

3: NaOMe / methanol / 24 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;
DOI:10.1021/jo00057a021

Reference yield:

: 143836-18-4,143836-19-5
benzyl 2-O-benzoyl-4,6-O-<(S)-1-methoxycarbonylethylidene>-3-O-methyl-α-D-glucopyranoside

: 1054630-28-2
(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / H₂ / 10 percent Pd/C / acetic acid / 16 h / 757.6 Torr / Ambient temperature

2: 99 percent / Na₂CO₃ / CH₂Cl₂ / 16 h / Ambient temperature

3: 70 percent / TMSOTf / CH₂Cl₂ / 2 h / -20 °C

4: 24 percent / ZnCl₂, dichloromethyl methyl ether / CHCl₃ / 3 h / 70 °C

5: 65 percent / AgOTf, 3-Angstroem molecular sieves / CH₂Cl₂ / 0.25 h / Ambient temperature

6: NaOMe / methanol / 24 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; Dichloromethyl methyl ether; 3 A molecular sieve; hydrogen; sodium methylate; silver trifluoromethanesulfonate; sodium carbonate; zinc(II) chloride; palladium on activated charcoal; In methanol; dichloromethane; chloroform; acetic acid;
DOI:10.1021/jo00057a021