(3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-one

Base Information

• Chemical Name: (3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-one
• CAS No.: 1417405-42-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• Mol file: 1417405-42-5.mol

Synonyms:

Chemical Property of (3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-one

There total 5 articles about (3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-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:

(3S,6R)-3-(benzyloxy)-6-(vinyloxy)-3,6-dihydro-2H-pyran (1417405-17-4) → (3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-one (1417405-42-5)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-dimethyl-aniline / nitrobenzene / 150 - 170 °C / Inert atmosphere

2: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol / 0.5 h / 20 - 30 °C / Inert atmosphere

3: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

4: toluene-4-sulfonic acid / dichloromethane / 10 h / Inert atmosphere; Reflux

With sodium chlorite; sodium dihydrogenphosphate; toluene-4-sulfonic acid; ozone; N,N-dimethyl-aniline; In dichloromethane; nitrobenzene; tert-butyl alcohol; 1: |Claisen Rearrangement;

DOI:10.1002/ejoc.201200898

Reference yield:

C20H22O3Se → (3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-one (1417405-42-5)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium periodate; sodium hydrogencarbonate / methanol; water / 1 h / Inert atmosphere

2: diisopropylamine / benzene / 0.5 h / Inert atmosphere; Reflux

3: N,N-dimethyl-aniline / nitrobenzene / 150 - 170 °C / Inert atmosphere

4: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol / 0.5 h / 20 - 30 °C / Inert atmosphere

5: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

6: toluene-4-sulfonic acid / dichloromethane / 10 h / Inert atmosphere; Reflux

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; N,N-dimethyl-aniline; diisopropylamine; In methanol; dichloromethane; water; nitrobenzene; tert-butyl alcohol; benzene; 3: |Claisen Rearrangement;

DOI:10.1002/ejoc.201200898

Reference yield:

C14H16O6 → (3aR,4S,6aR)-4-(benzyloxy)-perhydrofuro[2,3-b]furan-2(6aH)-one (1417405-42-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 10h; diastereoselective reaction; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201200898

upstream raw materials:

2-[(3S,4S)-3-(benzyloxy)-3,4-dihydro-2H-pyran-4-yl]acetaldehyde

2-[(3S,4S)-3-(benzyloxy)-3,4-dihydro-2H-pyran-4-yl]acetic acid

(3S,6R)-3-(benzyloxy)-6-(vinyloxy)-3,6-dihydro-2H-pyran