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

Base Information

• Chemical Name: 7-Oxabicyclo[4.1.0]hept-3-en-2-one, 5-hydroxy-4-(hydroxymethyl)-3-(1-methyl-1-propenyl)-, (1R,5S,6R)- (9CI)
• CAS No.: 635678-67-0
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• Mol file: 635678-67-0.mol

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

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

Chemical Property:

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)-3-(1-methyl-1-propenyl)-, (1R,5S,6R)- (9CI)

There total 10 articles about 7-Oxabicyclo[4.1.0]hept-3-en-2-one, 5-hydroxy-4-(hydroxymethyl)-3-(1-methyl-1-propenyl)-, (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:

6,6-dimethyl-3-(1-methyl-propenyl)-7a,7b-dihydro-1aH,4H-1,5,7-trioxa-cyclopropa[a]naphthalen-2-one (635678-64-7) → RKTS-34 (635678-67-0)

Guidance literature:

With Amberlyst 15; In methanol; at 20 ℃;

DOI:10.1016/j.bmcl.2003.08.003

Reference yield:

methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate (78844-86-7) → RKTS-34 (635678-67-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 96 percent / TBHP; VO(acac)2 / CH₂Cl₂ / Heating

2.1: NaBH₄ / methanol / 0 - 20 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

4.2: 100 percent / silica gel / toluene / 60 °C

5.1: 71 percent / Amberlyst 15 / propan-2-ol / 20 °C

6.1: PPTS / CH₂Cl₂ / 40 °C

7.1: I₂; PhI(OCOCF₃)2; pyridine / BHT / CH₂Cl₂ / 20 °C

8.1: Pd(PhCN)2Cl₂; Ph₃As; Ag₂O / tetrahydrofuran; H₂O / 20 °C

9.1: Amberlyst 15 / methanol / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; bis(benzonitrile)palladium(II) dichloride; Amberlyst 15; bis(acetylacetonate)oxovanadium; triphenyl-arsane; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; silver(l) oxide; 2,6-di-tert-butyl-4-methyl-phenol; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; 8.1: Suzuki coupling;

DOI:10.1016/j.bmcl.2003.08.003

Reference yield:

rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol (78844-86-7,78961-89-4,83648-86-6,90866-42-5,90866-43-6) → RKTS-34 (635678-67-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 49 percent / Pseudomonas stutzeri lipase (Meito TL)

2.1: 96 percent / TBHP; VO(acac)2 / CH₂Cl₂ / Heating

3.1: NaBH₄ / methanol / 0 - 20 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

5.2: 100 percent / silica gel / toluene / 60 °C

6.1: 71 percent / Amberlyst 15 / propan-2-ol / 20 °C

7.1: PPTS / CH₂Cl₂ / 40 °C

8.1: I₂; PhI(OCOCF₃)2; pyridine / BHT / CH₂Cl₂ / 20 °C

9.1: Pd(PhCN)2Cl₂; Ph₃As; Ag₂O / tetrahydrofuran; H₂O / 20 °C

10.1: Amberlyst 15 / methanol / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; bis(benzonitrile)palladium(II) dichloride; Amberlyst 15; bis(acetylacetonate)oxovanadium; triphenyl-arsane; Pseudomonas stutzeri lipase (Meito TL); iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; silver(l) oxide; 2,6-di-tert-butyl-4-methyl-phenol; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; 9.1: Suzuki coupling;

DOI:10.1016/j.bmcl.2003.08.003

upstream raw materials:

6,6-dimethyl-3-(1-methyl-propenyl)-7a,7b-dihydro-1aH,4H-1,5,7-trioxa-cyclopropa[a]naphthalen-2-one

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

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

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