6-Oxabicyclo[3.1.0]hexane-2-ethanol,4,4-difluoro-3-hydroxy-,(1-alpha-,2-bta-,3-bta-,5-alpha-)-(9CI)

Base Information

• Chemical Name: 6-Oxabicyclo[3.1.0]hexane-2-ethanol,4,4-difluoro-3-hydroxy-,(1-alpha-,2-bta-,3-bta-,5-alpha-)-(9CI)
• CAS No.: 73313-51-6
• Molecular Formula: C₇H₁₀F₂O₃
• Molecular Weight: 180.151
• Mol file: 73313-51-6.mol

Synonyms:6-Oxabicyclo[3.1.0]hexane-2-ethanol,4,4-difluoro-3-hydroxy-, (1a,2b,3b,5a)- (9CI); 6-Oxabicyclo[3.1.0]hexane-2-ethanol, 4,4-difluoro-3-hydroxy-, (1a,2b,3b,5a)-(?à)-

Chemical Property of 6-Oxabicyclo[3.1.0]hexane-2-ethanol,4,4-difluoro-3-hydroxy-,(1-alpha-,2-bta-,3-bta-,5-alpha-)-(9CI)

Chemical Property:

• PSA: 52.99000
• LogP: -0.23780

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Oxabicyclo[3.1.0]hexane-2-ethanol,4,4-difluoro-3-hydroxy-,(1-alpha-,2-bta-,3-bta-,5-alpha-)-(9CI)

There total 1 articles about 6-Oxabicyclo[3.1.0]hexane-2-ethanol,4,4-difluoro-3-hydroxy-,(1-alpha-,2-bta-,3-bta-,5-alpha-)-(9CI) 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: 87.0%

(1aS,1bR,4aR,5aS)-5,5-Difluoro-hexahydro-1,4-dioxa-cyclopropa[a]pentalen-3-one (73313-50-5,73347-05-4,73365-08-9) → (1S,3R,4S,5S)-2,2-Difluoro-4-(2-hydroxy-ethyl)-6-oxa-bicyclo[3.1.0]hexan-3-ol (73313-51-6,79390-93-5,79390-94-6)

Guidance literature:

With lithium aluminium tetrahydride; at -40 ℃; for 3h;

DOI:10.1021/jm00177a003

Reference yield:

(1S,3R,4S,5S)-2,2-Difluoro-4-(2-hydroxy-ethyl)-6-oxa-bicyclo[3.1.0]hexan-3-ol (73313-51-6,79390-93-5,79390-94-6) → 10,10-difluoro-13-dehydroprostacyclin methyl ester (73313-59-4,73347-11-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / toluene; hexane / 3 h / 55 °C

2: 75 percent / O₂ / Pt / acetone; H₂O

3: 91 percent / i-Bu₂AlH / hexane; toluene / -70 °C

4: 77 percent / 1 h / 25 °C

5: diethyl ether; methanol

6: 81 percent / I₂, NaHCO₃ / diethyl ether / 3.5 h / 0 °C

7: 78 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 0.5 h / 90 °C

With iodine; oxygen; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; platinum; In methanol; diethyl ether; hexane; water; acetone; toluene;

DOI:10.1021/jm00177a003

upstream raw materials:

(1aS,1bR,4aR,5aS)-5,5-Difluoro-hexahydro-1,4-dioxa-cyclopropa[a]pentalen-3-one

Downstream raw materials:

10,10-difluoro-13-dehydroprostacyclin methyl ester