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

Base Information

Chemical Name:ethyl (2S,3S,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate
CAS No.:874896-61-4
Molecular Formula:C₁₈H₂₆O₇
Molecular Weight:354.4
Hs Code.:

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

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Chemical Property of ethyl (2S,3S,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate

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Technology Process of ethyl (2S,3S,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate

There total 6 articles about ethyl (2S,3S,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate 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:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / silver(I) oxide; potassium iodide / CH₂Cl₂ / 3 h / 20 °C

2: 95 percent / lithium borohydride / methanol; diethyl ether / 2 h / 0 °C

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

4: sodium hydride / benzene / 20 °C

5: 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; lithium borohydride; oxalyl dichloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; potassium iodide; silver(l) oxide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene; 3: Swern oxidation / 4: Horner-Emmons reaction / 5: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo0521192

Reference yield:

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

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

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: 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