(2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone
CAS No.:161364-90-5
Molecular Formula:C₃₀H₃₂O₈
Molecular Weight:520.579
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

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Chemical Property of (2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

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Technology Process of (2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

There total 16 articles about (2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone 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: 75.0%

: 167394-67-4
Acetic acid (3S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-(2Z)-ylidenemethyl ester

: 161364-90-5
(2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

Guidance literature:: With mercury(II) diacetate; sodium chloride; In acetone; for 20h; Ambient temperature;
DOI:10.1016/S0040-4039(98)00737-0

Reference yield: 7.0%

: methyl 6-O-acetyl-2,3-bis-O-(phenylmethyl)-4-O-[(4-methoxyphenyl)methyl]-α-D-gluco-5-enpyranoside

: (2R,3S,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

: 161364-90-5
(2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

Guidance literature:: With sodium acetate; mercury(II) trifluoroacetate; In water; acetone; at 20 ℃; for 4h; Overall yield = 50 %; Inert atmosphere;
DOI:10.1016/j.tetlet.2016.06.038

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 161364-90-5
(2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone

Guidance literature:: Multi-step reaction with 6 steps

1: p-toluenesulfonic acid / dimethylformamide / 6 h / 65 °C

2: NaH / dimethylformamide / 5 h / Ambient temperature

3: 95 percent / lithium aluminum hydride, aluminum chloride / diethyl ether; CH₂Cl₂ / 3 h / 0 °C

4: 1.) (COCl)2, DMSO; 2.) Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

5: K₂CO₃ / acetonitrile / 20 h / Ambient temperature

6: 75 percent / mercuric acetate, aq. NaCl / acetone / 20 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; mercury(II) diacetate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1016/S0040-4039(98)00737-0