((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

Base Information

• Chemical Name: ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol
• CAS No.: 432036-83-4
• Molecular Formula: C₁₈H₂₀O₃
• Molecular Weight: 284.355
• Mol file: 432036-83-4.mol

Synonyms:((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

Chemical Property of ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

There total 20 articles about ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol 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: 91.0%

(-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-82-3) → ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol (432036-83-4) + (-)-camphanic acid (67111-66-4,13429-83-9)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20 - 25 ℃; for 1h; Large scale;

DOI:10.1021/op3003085

Reference yield:

5-benzyloxy-1,2,3,4-tetrahydro-naphthalen-1-one (90401-60-8) → ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol (432036-83-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium tetrahydroborate / toluene; ethanol / 1 h / 5 - 30 °C / Large scale

2.1: potassium hydrogensulfate / toluene / 1 h / Reflux; Large scale

3.1: 3-chloro-benzenecarboperoxoic acid / toluene / 1.5 h / 5 - 30 °C / Large scale

4.1: potassium hydroxide; water / dimethyl sulfoxide

5.1: toluene-4-sulfonic acid / toluene

6.1: trimethylsulfoxonium iodide; potassium tert-butylate / toluene / 2 h / 20 - 80 °C / Large scale

6.2: Large scale

7.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 3 h / 20 - 35 °C / Large scale

8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Large scale

9.1: ethanol / 20 - 80 °C / Resolution of racemate; Large scale

10.1: water; sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 - 25 °C / Large scale

With dmap; sodium tetrahydroborate; potassium hydrogensulfate; potassium tert-butylate; water; trimethylsulfoxonium iodide; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/op3003085

Reference yield:

5-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-ol (211805-74-2) → ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol (432036-83-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium hydrogensulfate / toluene / 1 h / Reflux; Large scale

2.1: 3-chloro-benzenecarboperoxoic acid / toluene / 1.5 h / 5 - 30 °C / Large scale

3.1: toluene-4-sulfonic acid / toluene / 1 h / 85 - 90 °C / Large scale

4.1: trimethylsulfoxonium iodide; potassium tert-butylate / toluene / 2 h / 20 - 80 °C / Large scale

4.2: Large scale

5.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 3 h / 20 - 35 °C / Large scale

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Large scale

7.1: ethanol / 20 - 80 °C / Resolution of racemate; Large scale

8.1: water; sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 - 25 °C / Large scale

With dmap; potassium hydrogensulfate; potassium tert-butylate; water; trimethylsulfoxonium iodide; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene; 3.1: |Meinwald Rearrangement;

DOI:10.1021/op3003085

upstream raw materials:

4-benzyloxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirane

5-benzyloxy-1,2,3,4-tetrahydro-2-oxonaphthalene

5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane]

(5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

Downstream raw materials:

diphenylcarbamic acid ((2R)-2,5-dihydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl ester

(2R)-2-hydroxy-2-(N,N-diphenylcarbamoyloxymethyl)-5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydronaphthalene

diphenylcarbamic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester