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
Hs Code.:
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;

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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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:

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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%

: 488808-29-3
(1R,5S,6R)-4-(tert-butyldimethylsiloxymethyl)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one

: 635678-66-9
(2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one

Guidance literature:: With Amberlyst 15; In isopropyl alcohol; at 20 ℃;
DOI:10.1016/j.bmcl.2003.08.003

Reference yield: 70.0%

: 1253855-97-8
(+)-phyllostine

: 635678-66-9
(2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; stereoselective reaction; Inert atmosphere;
DOI:10.5012/bkcs.2010.31.04.1047

Reference yield:

: 78844-86-7
methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate

: 635678-66-9
(2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one

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