(1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol

Base Information

• Chemical Name: (1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol
• CAS No.: 860267-60-3
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• Mol file: 860267-60-3.mol

Synonyms:(1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol

Chemical Property of (1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol

There total 3 articles about (1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol 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: 74.0%

3-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde + trimethyl orthoformate (149-73-5) → (1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol (860267-60-3)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In methanol; at 0 ℃; for 18h;

DOI:10.1021/ol0508126

Reference yield:

(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane (860267-59-0) → (1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol (860267-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

2: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

With sodium periodate; (1S)-10-camphorsulfonic acid; osmium(VIII) oxide; In tetrahydrofuran; methanol; water; tert-butyl alcohol; 1: Lemieux-Johnson oxidation;

DOI:10.1021/ol0508126

Reference yield:

Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (133842-56-5) → (1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol (860267-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CuBr / diethyl ether / 0.25 h / 0 °C

1.2: 11.2 g / diethyl ether / 2.5 h / 0 °C

2.1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

3.1: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

With sodium periodate; (1S)-10-camphorsulfonic acid; copper(I) bromide; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; water; tert-butyl alcohol; 2.1: Lemieux-Johnson oxidation;

DOI:10.1021/ol0508126

upstream raw materials:

trimethyl orthoformate

(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Downstream raw materials:

(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

(1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol

(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester