(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate

Base Information

• Chemical Name: (2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate
• CAS No.: 1314025-11-0
• Molecular Formula: C₂₆H₃₆O₅
• Molecular Weight: 428.569
• Mol file: 1314025-11-0.mol

Synonyms:(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate

Chemical Property of (2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate

There total 4 articles about (2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate 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: 89.0%

(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-(3-hydroxy-propyl)-3-methyltetrahydrofuran-3-yl acetate (1314025-10-9) → (2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate (1314025-11-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/ol201498g

Reference yield:

(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-[3-(4-methoxybenzyloxy)-propyl]-3-methyltetrahydrofuran-3-ol (1314025-09-6) → (2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate (1314025-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C

3: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C

With dmap; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; 3: Dess-Martin oxidation;

DOI:10.1021/ol201498g

Reference yield:

5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-[3-(4-methoxybenzyloxy)-propyl]dihydrofuran-3(2H)-one → (2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate (1314025-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether; toluene / -78 - 20 °C / Inert atmosphere

2: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C

4: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C

With dmap; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; toluene; 4: Dess-Martin oxidation;

DOI:10.1021/ol201498g

upstream raw materials:

(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-[3-(4-methoxybenzyloxy)-propyl]-3-methyltetrahydrofuran-3-ol

(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-[3-(4-methoxybenzyloxy)-propyl]-3-methyltetrahydrofuran-3-yl acetate

(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-(3-hydroxy-propyl)-3-methyltetrahydrofuran-3-yl acetate

Downstream raw materials:

(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-(4-diazo-3-oxo-butyl)-3-methyltetrahydrofuran-3-yl acetate

(1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

C₂₆H₃₆O₆