(2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester
CAS No.:215303-24-5
Molecular Formula:C₂₉H₃₂O₇
Molecular Weight:492.569
Hs Code.:

Synonyms:(2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester

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Chemical Property of (2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester

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Technology Process of (2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester

There total 8 articles about (2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester 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: 88.0%

: 215303-23-4
(2R,3R)-3-[(1R,2S,3R)-1,2,3-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-butyl]-oxirane-2-carboxylic acid methyl ester

: 215303-24-5
(2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester

Guidance literature:: With hydrogen fluoride; In acetonitrile; at -20 - -10 ℃; for 2.5h;
DOI:10.1021/jo981211d

Reference yield:

: 13263-74-6
D-xylose diethyl dithioacetal

: 215303-24-5
(2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / imidazole / CH₂Cl₂ / 3 h

2: 1.) NaH, 2.) n-Bu₄N(+)*I(-) / 1) THF, rt, 1.5 h; 2) THF, rt, 8 h

3: 77 percent / HgO, HgCl₂ / acetone; H₂O / 5 h / Heating

4: 86 percent / CH₂Cl₂ / 10 h

5: (DHQD)2-PHAL, K₃Fe(CN)6, K₂CO₃, CH₃SO₂NH₂, OsO₄, H₂O / 2-methyl-propan-2-ol / 36 h / 0 °C

6: 1.) sodium bis(trimethylsilyl)amide, 2.) p-nitrosulfonyl chloride, 3.) K₂CO₃ / 1) THF, -78 deg C, 20 min; 2) THF, -78 to -40 deg C, 50 min; 3) CH₃OH, 0 --> 25 deg C, 1.5 h

7: 88 percent / HF / acetonitrile / 2.5 h / -20 - -10 °C

With 1H-imidazole; osmium(VIII) oxide; methanesulfonamide; p-nitrosulfonyl chloride; hydrogen fluoride; water; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; mercury dichloride; mercury(II) oxide; potassium hexacyanoferrate(III); In dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo981211d

Reference yield:

: 100-39-0
benzyl bromide

: 215303-24-5
(2R,3R)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH, 2.) n-Bu₄N(+)*I(-) / 1) THF, rt, 1.5 h; 2) THF, rt, 8 h

2: 77 percent / HgO, HgCl₂ / acetone; H₂O / 5 h / Heating

3: 86 percent / CH₂Cl₂ / 10 h

4: (DHQD)2-PHAL, K₃Fe(CN)6, K₂CO₃, CH₃SO₂NH₂, OsO₄, H₂O / 2-methyl-propan-2-ol / 36 h / 0 °C

5: 1.) sodium bis(trimethylsilyl)amide, 2.) p-nitrosulfonyl chloride, 3.) K₂CO₃ / 1) THF, -78 deg C, 20 min; 2) THF, -78 to -40 deg C, 50 min; 3) CH₃OH, 0 --> 25 deg C, 1.5 h

6: 88 percent / HF / acetonitrile / 2.5 h / -20 - -10 °C

With osmium(VIII) oxide; methanesulfonamide; p-nitrosulfonyl chloride; hydrogen fluoride; water; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; mercury dichloride; mercury(II) oxide; potassium hexacyanoferrate(III); In dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo981211d