((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

Base Information

Chemical Name:((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid
CAS No.:215303-38-1
Molecular Formula:C₂₉H₃₀O₆
Molecular Weight:474.554
Hs Code.:

Synonyms:((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

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Chemical Property of ((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

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Technology Process of ((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

There total 12 articles about ((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic 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: 94.0%

: 201603-56-7
((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

: 215303-38-1
((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran;
DOI:10.1021/jo981211d

Reference yield:

: 100-39-0
benzyl bromide

: 215303-38-1
((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

Guidance literature:: Multi-step reaction with 12 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: 80 percent / ((μ-chloro)(μ-methylene)dimethylaluminum / pyridine; toluene; tetrahydrofuran / 2 h / -78 - -15 °C

6: 88 percent / n-Bu₄N(+)*F(-) / tetrahydrofuran / 2 h / Ambient temperature

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

8: 1.) CuI, 2.) chlorotrimethylsilane / 1) THF, -78 deg C, 40 min; 2) THF, -78 deg C, 2 h

9: 94 percent / bis(tricyclohexylphosphine)benzylideneruthenium dichloride / CH₂Cl₂ / 60 h / Ambient temperature

10: 1.) LiOH, 2.) KHCO₃, KI, I₂ / 1) water, 4 h; 2) water, 6 h

11: 98 percent / Na₂CO₃ / 8 h / Ambient temperature

12: 94 percent / aq. LiOH / tetrahydrofuran

With lithium hydroxide; copper(l) iodide; osmium(VIII) oxide; Grubbs catalyst first generation; chloro-trimethyl-silane; oxalyl dichloride; methanesulfonamide; (μ-chloro)(μ-methylene)dimethylaluminum; tetrabutyl ammonium fluoride; water; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; potassium carbonate; potassium hydrogencarbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium iodide; mercury dichloride; mercury(II) oxide; potassium hexacyanoferrate(III); In tetrahydrofuran; pyridine; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/jo981211d

Reference yield:

: 185987-56-8
2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal

: 215303-38-1
((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 86 percent / CH₂Cl₂ / 10 h

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

3: 80 percent / ((μ-chloro)(μ-methylene)dimethylaluminum / pyridine; toluene; tetrahydrofuran / 2 h / -78 - -15 °C

4: 88 percent / n-Bu₄N(+)*F(-) / tetrahydrofuran / 2 h / Ambient temperature

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

6: 1.) CuI, 2.) chlorotrimethylsilane / 1) THF, -78 deg C, 40 min; 2) THF, -78 deg C, 2 h

7: 94 percent / bis(tricyclohexylphosphine)benzylideneruthenium dichloride / CH₂Cl₂ / 60 h / Ambient temperature

8: 1.) LiOH, 2.) KHCO₃, KI, I₂ / 1) water, 4 h; 2) water, 6 h

9: 98 percent / Na₂CO₃ / 8 h / Ambient temperature

10: 94 percent / aq. LiOH / tetrahydrofuran

With lithium hydroxide; copper(l) iodide; osmium(VIII) oxide; Grubbs catalyst first generation; chloro-trimethyl-silane; oxalyl dichloride; methanesulfonamide; (μ-chloro)(μ-methylene)dimethylaluminum; tetrabutyl ammonium fluoride; water; iodine; sodium carbonate; potassium carbonate; potassium hydrogencarbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium iodide; potassium hexacyanoferrate(III); In tetrahydrofuran; pyridine; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo981211d