7-Oxabicyclo[4.1.0]hept-3-en-2-one, 5-hydroxy-4-(hydroxymethyl)-, (1R,5S,6R)- (9CI)

Base Information

• Chemical Name: 7-Oxabicyclo[4.1.0]hept-3-en-2-one, 5-hydroxy-4-(hydroxymethyl)-, (1R,5S,6R)- (9CI)
• CAS No.: 635678-66-9
• Molecular Formula: C₇H₈O₄
• Molecular Weight: 156.138
• Mol file: 635678-66-9.mol

Synonyms:RKTS-33;(1R,5S,6R)-5-Hydroxy-4-hydroxymethyl-7-oxa-bicyclo[4.1.0]hept-3-en-2-one;

Chemical Property of 7-Oxabicyclo[4.1.0]hept-3-en-2-one, 5-hydroxy-4-(hydroxymethyl)-, (1R,5S,6R)- (9CI)

Chemical Property:

• PSA: 70.06000
• LogP: -1.38390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Oxabicyclo[4.1.0]hept-3-en-2-one, 5-hydroxy-4-(hydroxymethyl)-, (1R,5S,6R)- (9CI)

There total 14 articles about 7-Oxabicyclo[4.1.0]hept-3-en-2-one, 5-hydroxy-4-(hydroxymethyl)-, (1R,5S,6R)- (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: 71.0%

(1R,5S,6R)-4-(tert-butyldimethylsiloxymethyl)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one (488808-29-3) → (2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one (635678-66-9)

Guidance literature:

With Amberlyst 15; In isopropyl alcohol; at 20 ℃;

DOI:10.1016/j.bmcl.2003.08.003

Reference yield: 70.0%

(+)-phyllostine (1253855-97-8) → (2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one (635678-66-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.5012/bkcs.2010.31.04.1047

Reference yield:

methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate (78844-86-7) → (2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one (635678-66-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / tert-butyl hydroperoxide / VO(acac)2 / CH₂Cl₂; toluene / 12 h / Heating

2: 96 percent / NaBH₄ / methanol / 0 - 20 °C

3: 84 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / 20 °C

4: TEMPO; NaOCl; NaHCO₃ / KBr / CH₂Cl₂; H₂O / 0.67 h / -10 °C

5: 84.7 mg / silica gel / toluene / 4.5 h / 70 °C

6: MeOH; Amberlyst 15 / 5 h / 20 °C

With methanol; tert.-butylhydroperoxide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; Amberlyst 15; silica gel; sodium hydrogencarbonate; triethylamine; bis(acetylacetonate)oxovanadium; potassium bromide; In methanol; dichloromethane; water; toluene;

DOI:10.1021/jo048425h

upstream raw materials:

(1R,5S,6R)-4-(tert-butyldimethylsiloxymethyl)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one

methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate

rac-(1R,2R,3R,6R,7S)-2-iodo-4,8-dioxatricyclo[4.2.1.0^3,7]nonan-5-one

rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol

Downstream raw materials:

RKTS-34