(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

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
CAS No.:1055030-33-5
Molecular Formula:C₂₉H₄₃NO₁₅
Molecular Weight:645.658
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

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

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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

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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

There total 13 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 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

: 1055030-33-5
(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

Guidance literature:: Multi-step reaction with 4 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

4: 1 M aq. NaOH / H₂O; methanol / 24 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane; water;
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

: 1055030-33-5
(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

Guidance literature:: Multi-step reaction with 7 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

7: 1 M aq. NaOH / H₂O; methanol / 24 h / Ambient temperature

With sodium hydroxide; 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; water; acetic acid;
DOI:10.1021/jo00057a021