(7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one

Base Information

• Chemical Name: (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one
• CAS No.: 118533-10-1
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.262
• Mol file: 118533-10-1.mol

Synonyms:(7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one

Chemical Property of (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one

There total 6 articles about (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one 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: 60.0%

[(3aS,7aR)-6-Benzyloxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-(7E)-ylidene]-acetic acid methyl ester (118533-09-8,118533-11-2) → (4RS, 7S, 7aR)-4,7-dihydroxy-7,7a-dihydrofuro<3,2-c>pyran-2(4H, 6H)-one (118533-12-3,118626-84-9) + (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one (118533-10-1)

Guidance literature:

With perchloric acid; In tetrahydrofuran; water; for 1.25h; Heating;

DOI:10.1016/0040-4039(88)85235-3

Reference yield:

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one (118533-10-1)

Guidance literature:

Multi-step reaction with 5 steps

1: HCl

2: sulphuric acid

3: 66 percent

4: triphenylphosphine, propylene oxid / CH₂Cl₂

5: 33 percent / HClO₄ / H₂O; tetrahydrofuran / 1.25 h / Heating

With hydrogenchloride; perchloric acid; sulfuric acid; triphenylphosphine; methyloxirane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/0040-4039(88)85235-3

Reference yield:

(3aS,7aS)-6-Benzyloxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one (28070-06-6,65247-32-7) → (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one (118533-10-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine, propylene oxid / CH₂Cl₂

2: 33 percent / HClO₄ / H₂O; tetrahydrofuran / 1.25 h / Heating

With perchloric acid; triphenylphosphine; methyloxirane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/0040-4039(88)85235-3

upstream raw materials:

[(3aS,7aR)-6-Benzyloxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-(7E)-ylidene]-acetic acid methyl ester

L-(+)-arabinose

(3aS,7aS)-6-Benzyloxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one

(3R,4S,5S)-2-Benzyloxy-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

(R)-O-benzylpatulin