(2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate

Base Information

Chemical Name:(2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate
CAS No.:166945-71-7
Molecular Formula:C₂₉H₃₈O₈
Molecular Weight:514.616
Hs Code.:

Synonyms:(2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate

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Chemical Property of (2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate

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Technology Process of (2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate

There total 4 articles about (2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate 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: 48.0%

: 100-39-0
benzyl bromide

: 166945-70-6
(2R,3S,4R,5S,6R)-Ethyl 4,5:6,7-bis-O-(1-methylethylidene)-2,3-dihydroxyheptanoate

: (2R,3S)-2-Benzyloxy-3-hydroxy-3-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propionic acid ethyl ester

: (2R,3R)-3-Benzyloxy-2-hydroxy-3-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propionic acid ethyl ester

: 166945-71-7
(2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate

Guidance literature:: With dibenzo-18-crown-6; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; Title compound not separated from byproducts; 1.) 0 deg C, 1 h, 2.) r.t., 3 h;
DOI:10.1021/jo00101a020

Reference yield:

: 65391-47-1
(E)-ethyl 3-((4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 166945-71-7
(2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / K₃Fe(CN)6, K₂CO₃, CH₃SO₂NH₂, (DHQ)2-PHAL, OsO₄ / 2-methyl-propan-2-ol; H₂O / 25 h / 0 °C

2: 48 percent / NaH, Bu₄NI, dibenzo-18-crown-6 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 3 h

With osmium(VIII) oxide; dibenzo-18-crown-6; (DHQ)2-PHAL; methanesulfonamide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.1021/jo00101a020

Reference yield:

: 38145-93-6
1,2:3,4-di-O-isopropylidene-D-mannitol

: 166945-71-7
(2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate

Guidance literature:: Multi-step reaction with 4 steps

1: NaIO₄

2: NaH / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) 0 deg C to r.t., 2 h

3: 93 percent / K₃Fe(CN)6, K₂CO₃, CH₃SO₂NH₂, (DHQ)2-PHAL, OsO₄ / 2-methyl-propan-2-ol; H₂O / 25 h / 0 °C

4: 48 percent / NaH, Bu₄NI, dibenzo-18-crown-6 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 3 h

With sodium periodate; osmium(VIII) oxide; dibenzo-18-crown-6; (DHQ)2-PHAL; methanesulfonamide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.1021/jo00101a020