(1S,6α)-1α-(Benzoyloxy)methyl-7-oxabicyclo[4.1.0]hept-4-ene-2β,3α-diol 3-benzoate

Base Information

• Chemical Name: (1S,6α)-1α-(Benzoyloxy)methyl-7-oxabicyclo[4.1.0]hept-4-ene-2β,3α-diol 3-benzoate
• CAS No.: 29399-87-9
• Molecular Formula: C21H18 O6
• Molecular Weight: 366.36402
• Mol file: 29399-87-9.mol

Synonyms:7-Oxabicyclo[4.1.0]hept-4-ene-2,3-diol,1-(hydroxymethyl)-, 1,3-dibenzoate, (+)- (8CI);7-Oxabicyclo[4.1.0]hept-4-ene-2,3-diol, 1-[(benzoyloxy)methyl]-, 3-benzoate,[1S-(1a,2b,3a,6a)]-; (+)-Pipoxide; Pipoxide

Chemical Property of (1S,6α)-1α-(Benzoyloxy)methyl-7-oxabicyclo[4.1.0]hept-4-ene-2β,3α-diol 3-benzoate

Chemical Property:

• PSA: 85.36000
• LogP: 2.13730

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,6α)-1α-(Benzoyloxy)methyl-7-oxabicyclo[4.1.0]hept-4-ene-2β,3α-diol 3-benzoate

There total 17 articles about (1S,6α)-1α-(Benzoyloxy)methyl-7-oxabicyclo[4.1.0]hept-4-ene-2β,3α-diol 3-benzoate 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%

(2R)-trans-3-(benzoyloxy)-1-<(benzoyloxy)methyl>-2-hydroxycyclohexa-4,6-diene (85966-24-1) → (+)-Pipoxide (29399-87-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 0 ℃; for 1h;

DOI:10.1021/jo00213a030

Reference yield: 62.0%

((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate (78804-17-8) → (+)-Pipoxide (29399-87-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1039/a905631i

Reference yield:

benzoyl chloride (98-88-4) → (+)-Pipoxide (29399-87-9)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine; DMAP

2: NMO; OsO₄; H₂O / tetrahydrofuran / 20 °C

3: Zn; NH₄Cl; H₂O / tetrahydrofuran / Heating

4: dimethylformamide / 80 °C

5: Ph₂O / 0.25 h / Heating

6: HF / acetonitrile

7: 62 percent / DEAD; PPh₃ / tetrahydrofuran

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; diphenylether; hydrogen fluoride; water; ammonium chloride; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: Oxidation / 3: Ring cleavage / 4: Substitution / 5: Elimination / 6: Desilylation / 7: Dehydration;

DOI:10.1039/a905631i

upstream raw materials:

(2R)-trans-3-(benzoyloxy)-1-<(benzoyloxy)methyl>-2-hydroxycyclohexa-4,6-diene

((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate

benzoyl chloride

(+)-(1R,4S,4aR,5S,8aS)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one

Downstream raw materials:

C₂₁H₁₈O₆

C₂₁H₁₈O₆

(-)-(1S,2R,4R,5S,6R,7S)-4-benzoyloxymethyl-3,8-dioxatricyclo<5.1.0.0^2,4>octane-5,6-diol 6-benzoate

((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate

Refernces

• 1、 Hiroya, Kou,Ogasawara, Kunio. "The first enantiocontrolled synthesis of naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates (-)-zeylenol, (-)-uvarigranol G, (-)-tonkinenin A and (+)-pipoxide". . p. 2197 - 2198. Retrieved 2007/10/03.