(3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde

Base Information

Chemical Name:(3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde
CAS No.:286956-65-8
Molecular Formula:C₁₃H₁₆O₇
Molecular Weight:284.266
Hs Code.:

Synonyms:(3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde

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Chemical Property of (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde

Chemical Property:

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Technology Process of (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde

There total 7 articles about (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde 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: 45.0%

: 286956-64-7
(3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxy-N-methoxy-N-methylcyclohex-1-ene-1-carboxamide

: 286956-65-8
(3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde

Guidance literature:: With RedAl; In tetrahydrofuran; toluene; at -60 ℃; for 0.5h;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: 21967-35-1
(3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

: 286956-65-8
(3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 1.47 g / pyridine / 5 h

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

3: 250 mg / N-methylpiperidine / CH₂Cl₂ / -20 - 20 °C

4: 45 percent / dihydro-bis(2-methoxyethoxy)aluminate / tetrahydrofuran; toluene / 0.5 h / -60 °C

With pyridine; N-methylcyclohexylamine; RedAl; In tetrahydrofuran; dichloromethane; toluene; 1: Acetylation / 2: Condensation / 3: Substitution / 4: Reduction;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

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

: 286956-65-8
(3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 2 h / 20 °C

2: 94 percent / aq. AcOH / 3 h / 60 - 70 °C

3: aq. NaOH / methanol / 48 h / 20 °C

4: 1.47 g / pyridine / 5 h

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

6: 250 mg / N-methylpiperidine / CH₂Cl₂ / -20 - 20 °C

7: 45 percent / dihydro-bis(2-methoxyethoxy)aluminate / tetrahydrofuran; toluene / 0.5 h / -60 °C

With pyridine; N-methylcyclohexylamine; sodium hydroxide; di-isopropyl azodicarboxylate; acetic acid; RedAl; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Mitsunobu reaction / 2: Hydrolysis / 3: Hydrolysis / 4: Acetylation / 5: Condensation / 6: Substitution / 7: Reduction;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8