(2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate

Base Information

Chemical Name:(2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate
CAS No.:215544-02-8
Molecular Formula:C₁₈H₂₆O₇
Molecular Weight:354.4
Hs Code.:

Synonyms:(2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate

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Chemical Property of (2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate

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Technology Process of (2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate

There total 3 articles about (2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate 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: 74.0%

: 90661-39-5
(E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 215544-02-8
(2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate

Guidance literature:: With osmium(VIII) oxide; methanesulfonamide; water; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 - 20 ℃;
DOI:10.1055/s-1998-6103

Reference yield:

: 848566-19-8
(E,4S,5S)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate

: 215544-02-8
(2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate

Guidance literature:: Multi-step reaction with 2 steps

1: CSA / CH₂Cl₂ / 3 h / 20 °C

2: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O; CH₂Cl₂ / 0 - 20 °C

With methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol050044i

Reference yield:

: 144895-69-2
(3E,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate

: 215544-02-8
(2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate

Guidance literature:: Multi-step reaction with 3 steps

1: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol; H₂O / 0 - 20 °C

2: CSA / CH₂Cl₂ / 3 h / 20 °C

3: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O; CH₂Cl₂ / 0 - 20 °C

With methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 3: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol050044i