(2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid

Base Information

Chemical Name:(2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid
CAS No.:215303-18-7
Molecular Formula:C₃₁H₃₂O₈
Molecular Weight:532.59
Hs Code.:

Synonyms:(2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid

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Chemical Property of (2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid

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Technology Process of (2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid

There total 10 articles about (2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid 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: 85.0%

: 215303-26-7
(2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid methyl ester

: 215303-18-7
(2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; 1) 10 deg C --> rt, 2 h; 2) rt, 2 h;
DOI:10.1021/jo981211d

Reference yield:

: 13263-74-6
D-xylose diethyl dithioacetal

: 215303-18-7
(2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 9 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

8: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 40 min; 2) CH₂Cl₂, -78 to -30 deg C, 15 min; 3) CH₂Cl₂, -30 deg C --> rt, 6 h

9: 85 percent / aq. LiOH / tetrahydrofuran / 1) 10 deg C --> rt, 2 h; 2) rt, 2 h

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

Reference yield:

: 100-39-0
benzyl bromide

: 215303-18-7
(2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 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

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 40 min; 2) CH₂Cl₂, -78 to -30 deg C, 15 min; 3) CH₂Cl₂, -30 deg C --> rt, 6 h

8: 85 percent / aq. LiOH / tetrahydrofuran / 1) 10 deg C --> rt, 2 h; 2) rt, 2 h

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