Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

Base Information

Chemical Name:Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester
CAS No.:1053697-43-0
Molecular Formula:C₄₆H₄₆N₂O₇
Molecular Weight:738.88
Hs Code.:

Synonyms:Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

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Chemical Property of Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

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Technology Process of Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

There total 11 articles about Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl 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:

: (3aS,4aS,7aR,8S,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-one

: 1053697-43-0
Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / 0 °C

1.2: 54 percent / tetrahydrofuran / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 50 °C

2.2: 42 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 1 h / 50 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.1: AcCl / CH₂Cl₂; methanol / 0.33 h

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 5 h

6.1: HCl / methanol / 24 h / 20 °C

7.1: Bu₂SnO / toluene / 2 h / Heating

7.2: 77 percent / CsF / toluene / -50 - 20 °C

8.1: NaH / dimethylformamide / 0.5 h / 0 °C

8.2: 99 percent / n-Bu₄NI

9.1: RhCl(PPh₃)3; DABCO / ethanol / 5 h / Heating

9.2: 100 percent / aq. HCl / acetone / 4 h / Heating

10.1: toluene / 0.67 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; RhCl(PPh₃)3; sodium hydride; di(n-butyl)tin oxide; acetyl chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Methylenation / 2.1: Hydroboration / 2.2: Oxidation / 3.1: Metallation / 3.2: Benzylation / 4.1: Acidolysis / 5.1: Metallation / 5.2: Benzylation / 6.1: Acidolysis / 7.1: Stannylation / 7.2: Allylation / 8.1: Metallation / 8.2: Benzylation / 9.1: Isomerization / 9.2: Acidolysis / 10.1: Carbonylation;
DOI:10.1021/jm000117y

Reference yield:

: 148983-67-9
1L-(1,2,4,6/3,5)-3,4,5-tri-O-benzyl-6-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

: 1053697-43-0
Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Bu₂SnO / toluene / 2 h / Heating

1.2: 77 percent / CsF / toluene / -50 - 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 99 percent / n-Bu₄NI

3.1: RhCl(PPh₃)3; DABCO / ethanol / 5 h / Heating

3.2: 100 percent / aq. HCl / acetone / 4 h / Heating

4.1: toluene / 0.67 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; RhCl(PPh₃)3; sodium hydride; di(n-butyl)tin oxide; In ethanol; N,N-dimethyl-formamide; toluene; 1.1: Stannylation / 1.2: Allylation / 2.1: Metallation / 2.2: Benzylation / 3.1: Isomerization / 3.2: Acidolysis / 4.1: Carbonylation;
DOI:10.1021/jm000117y

Reference yield:

: 192122-41-1
(3aR,4R,4aR,7aR,8S,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol

: 1053697-43-0
Imidazole-1-carboxylic acid (1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-benzyloxymethyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / 2 h / -78 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / 0 °C

2.2: 54 percent / tetrahydrofuran / -78 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 2 h / 50 °C

3.2: 42 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 1 h / 50 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.1: AcCl / CH₂Cl₂; methanol / 0.33 h

6.1: NaH / dimethylformamide / 0.5 h / 0 °C

6.2: 5 h

7.1: HCl / methanol / 24 h / 20 °C

8.1: Bu₂SnO / toluene / 2 h / Heating

8.2: 77 percent / CsF / toluene / -50 - 20 °C

9.1: NaH / dimethylformamide / 0.5 h / 0 °C

9.2: 99 percent / n-Bu₄NI

10.1: RhCl(PPh₃)3; DABCO / ethanol / 5 h / Heating

10.2: 100 percent / aq. HCl / acetone / 4 h / Heating

11.1: toluene / 0.67 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; RhCl(PPh₃)3; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; acetyl chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Oxidation / 2.1: Metallation / 2.2: Methylenation / 3.1: Hydroboration / 3.2: Oxidation / 4.1: Metallation / 4.2: Benzylation / 5.1: Acidolysis / 6.1: Metallation / 6.2: Benzylation / 7.1: Acidolysis / 8.1: Stannylation / 8.2: Allylation / 9.1: Metallation / 9.2: Benzylation / 10.1: Isomerization / 10.2: Acidolysis / 11.1: Carbonylation;
DOI:10.1021/jm000117y