methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

Base Information

Chemical Name:methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate
CAS No.:286956-61-4
Molecular Formula:C₂₁H₂₄O₆
Molecular Weight:372.418
Hs Code.:

Synonyms:methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

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Chemical Property of methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

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Technology Process of methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

There total 1 articles about methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate 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: 94.0%

: 123994-31-0
methyl (3S,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

: 65-85-0,8013-63-6
benzoic acid

: 286956-61-4
methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield: 94.0%

: 286956-61-4
methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

: 286956-62-5
methyl (3R,4R,5R)-3-O-benzoyl-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate

Guidance literature:: With acetic acid; at 60 - 70 ℃; for 3h;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: 286956-61-4
methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-{hydroxy-[(R)-phosphono-((3R,4R,5R)-3,4,5-triacetoxy-cyclohex-1-enyl)-methoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / aq. AcOH / 3 h / 60 - 70 °C

2: aq. NaOH / methanol / 48 h / 20 °C

3: 1.47 g / pyridine / 5 h

4: N-methylpiperidine / CH₂Cl₂ / -20 °C

5: 250 mg / N-methylpiperidine / CH₂Cl₂ / -20 - 20 °C

6: 45 percent / dihydro-bis(2-methoxyethoxy)aluminate / tetrahydrofuran; toluene / 0.5 h / -60 °C

7: Et₃N

8: tetrazole / CH₂Cl₂ / 3 h / 20 °C

9: tBuOOH / CH₂Cl₂ / 1 h

10: 60 mg

11: dimedone; Et₃N / Pd(PPh₃)4 / tetrahydrofuran / 4 h

With pyridine; 1H-tetrazole; N-methylcyclohexylamine; tert.-butylhydroperoxide; sodium hydroxide; dimedone; acetic acid; RedAl; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Hydrolysis / 2: Hydrolysis / 3: Acetylation / 4: Condensation / 5: Substitution / 6: Reduction / 7: Addition / 8: Condensation / 9: Oxidation / 10: Elimination / 11: ester cleavage;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8