(3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one

Base Information

Chemical Name:(3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one
CAS No.:852611-21-3
Molecular Formula:C₂₀H₂₂O₇
Molecular Weight:374.39
Hs Code.:

Synonyms:(3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one

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Chemical Property of (3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one

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Technology Process of (3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one

There total 7 articles about (3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one 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: 85.0%

: 852611-12-2
(2S,3S,4R,5S)-ethyl 4-(4-methoxyphenoxy)-6-(benzyloxy)-2,3,5-trihydroxyhexanoate

: 852611-21-3
(3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one

Guidance literature:: With pyridinium p-toluenesulfonate; In benzene; for 5h; Heating;
DOI:10.1016/j.tetlet.2005.03.029

Reference yield:

: (E)-ethyl 4-(4-methoxyphenoxy)-6-(benzyloxy)-5-hydroxyhex-2-enoate

: 852611-21-3
(3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: AD-mix-β / 2-methyl-propan-2-ol; H2O; CH2Cl2 / 0 °C

2: 85 percent / pyridinium toluenesulfonate / benzene / 5 h / Heating

With AD-mix-β; pyridinium p-toluenesulfonate; In dichloromethane; water; tert-butyl alcohol; benzene; 1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.carres.2006.03.024

Reference yield:

: 852611-09-7
(E,4S,5S)-ethyl 4-(4-methoxyphenoxy)-6-(benzyloxy)-5-hydroxyhex-2-enoate

: 852611-21-3
(3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / K₃Fe(CN)6; OsO₄; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O; CH₂Cl₂ / 0 °C

2: 85 percent / Py*TsOH / benzene / 5 h / Heating

With osmium(VIII) oxide; pyridinium p-toluenesulfonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol; benzene; 1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2005.03.029