(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

Base Information

Chemical Name:(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate
CAS No.:874896-62-5
Molecular Formula:C₁₈H₂₆O₇
Molecular Weight:354.4
Hs Code.:

Synonyms:(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

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Chemical Property of (2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

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Technology Process of (2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

There total 7 articles about (2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate 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: 90.0%

: 874896-58-9
(4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

: 874896-62-5
(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

: 874896-61-4
ethyl (2S,3S,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate

Guidance literature:: With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); (DHQD)2PHAL; methanesulfonamide; In water; tert-butyl alcohol; at 4 ℃; for 36h;
DOI:10.1021/jo0521192

Reference yield: 80.0%

: 874896-58-9
(4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

: 874896-62-5
(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

Guidance literature:: With potassium osmate(VI); methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 0 ℃; for 36h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetlet.2019.07.006

Reference yield:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 874896-62-5
(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

2: sodium hydride / benzene / 20 °C

3: 90 percent / potassium ferricyanide(III); potassium carbonate; osmium tetroxide / hydroquinine 1,4-phthalazinediyl diether; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 36 h / 4 °C

With osmium(VIII) oxide; oxalyl dichloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In dichloromethane; water; tert-butyl alcohol; benzene; 1: Swern oxidation / 2: Horner-Emmons reaction / 3: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo0521192