(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

Base Information

Chemical Name:(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one
CAS No.:274692-78-3
Molecular Formula:C₂₃H₂₆O₅
Molecular Weight:382.456
Hs Code.:

Synonyms:(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

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Chemical Property of (2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

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Technology Process of (2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

There total 3 articles about (2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one 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: 86.0%

: 274692-75-0
2,5-di-O-benzyl-1,6-O-isopropylidene-D-allo-inositol 3,4-cyclic sulfate

: 274692-78-3
(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

Guidance literature:: 2,5-di-O-benzyl-1,6-O-isopropylidene-D-allo-inositol 3,4-cyclic sulfate; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 1.5h;

With sulfuric acid; In tetrahydrofuran; water; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO;2-Z

Reference yield:

: 188839-35-2,173828-64-3
D-1,6-O-(1-methylethylidene)-2,5-bis-O-(phenylmethyl)-allo-inositol

: 274692-78-3
(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 99 mg / NaIO₄; ruthenium trichloride / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

3.1: tBuOK / tetrahydrofuran / 1.5 h / 20 °C

3.2: 86 percent / H₂SO₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

With ruthenium trichloride; sodium periodate; thionyl chloride; potassium tert-butylate; triethylamine; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile; 1.1: Condensation / 2.1: Oxidation / 3.1: Ring cleavage / 3.2: Elimination;
DOI:10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO;2-Z

Reference yield:

: (3aS,4S,4aR,7aR,8S,8aR)-4,8-Bis-benzyloxy-6,6-dimethyl-hexahydro-1,3,5,7-tetraoxa-2-thia-s-indacene 2-oxide

: 274692-78-3
(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 mg / NaIO₄; ruthenium trichloride / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

2.1: tBuOK / tetrahydrofuran / 1.5 h / 20 °C

2.2: 86 percent / H₂SO₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

With ruthenium trichloride; sodium periodate; potassium tert-butylate; In tetrahydrofuran; tetrachloromethane; water; acetonitrile; 1.1: Oxidation / 2.1: Ring cleavage / 2.2: Elimination;
DOI:10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO;2-Z