(4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one

Base Information

• Chemical Name: (4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one
• CAS No.: 210764-93-5
• Molecular Formula: C₂₄H₂₆O₇
• Molecular Weight: 426.466
• Mol file: 210764-93-5.mol

Synonyms:(4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one

Chemical Property of (4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one

There total 6 articles about (4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one 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: 84.0%

Acetic acid (1S,2R,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-6-oxo-cyclohexyl ester (222545-15-5) → (4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5)

Guidance literature:

With methanesulfonyl chloride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

methyl 4-O-acetyl-2,3-di-O-(4-methoxy)benzyl-α-D-xylo-hex-5-enopyranoside (210764-92-4) → (4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Hg(OCOCF₃)2 / acetone; H₂O / 15 h / Ambient temperature

2: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

With mercury(II) trifluoroacetate; methanesulfonyl chloride; In dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) room temperature, 20 h

2: 89 percent / AcOH / H₂O / 2 h / 60 °C

3: 93 percent / PPh₃, imidazole, I₂ / toluene / 5 h / Ambient temperature

4: 1.) t-BuOK, 2.) pyridine / 1.) THF, room temperature, 23 h, 2.) room temperature, 3 h

5: 100 percent / Hg(OCOCF₃)2 / acetone; H₂O / 15 h / Ambient temperature

6: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 1H-imidazole; potassium tert-butylate; iodine; mercury(II) trifluoroacetate; sodium hydride; acetic acid; methanesulfonyl chloride; triphenylphosphine; In dichloromethane; water; acetone; toluene;

DOI:10.1016/S0040-4020(99)00004-6

upstream raw materials:

Acetic acid (1S,2R,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-6-oxo-cyclohexyl ester

p-methoxybenzyl chloride

methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside

methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside

Downstream raw materials:

(1S,4S,5R,6R)-2-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-ol

(3S,3aR,4S,5S,7aR)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-octahydro-benzofuran-2-ol

(3S,3aS,4S,5S,7aR)-4,5-di-(4-methoxybenzyl)oxy-3-methyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

2-[(1S,5S,6S)-5,6-Bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl]-propionic acid