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

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-2,3-Bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptanol
CAS No.:166945-72-8
Molecular Formula:C₂₇H₃₆O₇
Molecular Weight:472.579
Hs Code.:

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

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

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

There total 5 articles about (2S,3S,4R,5R,6R)-2,3-Bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptanol 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: 95.0%

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

: 166945-72-8
(2S,3S,4R,5R,6R)-2,3-Bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptanol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 1h;
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

: 166945-72-8
(2S,3S,4R,5R,6R)-2,3-Bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptanol

Guidance literature:: Multi-step reaction with 3 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

3: 95 percent / DIBALH / tetrahydrofuran; hexane / 1 h / 0 °C

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

Reference yield:

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

: 166945-72-8
(2S,3S,4R,5R,6R)-2,3-Bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptanol

Guidance literature:: Multi-step reaction with 2 steps

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

2: 95 percent / DIBALH / tetrahydrofuran; hexane / 1 h / 0 °C

With dibenzo-18-crown-6; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane;
DOI:10.1021/jo00101a020