(3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene

Base Information

• Chemical Name: (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene
• CAS No.: 210764-95-7
• Molecular Formula: C₂₉H₃₆O₈
• Molecular Weight: 512.6

Synonyms:(3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene

Chemical Property of (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene

Chemical Property:

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Technology Process of (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene

There total 7 articles about (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene 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: 99.0%

3,4-dihydro-2H-pyran (110-87-2) + (1S,4S,5R,6R)-2-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-ol (210764-94-6) → (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene (210764-95-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1039/a802169d

Reference yield:

(4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5) → (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene (210764-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

2: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

With sodium tetrahydroborate; cerium(III) chloride; pyridinium p-toluenesulfonate; In methanol; dichloromethane;

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

Reference yield:

Acetic acid (1S,2R,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-6-oxo-cyclohexyl ester (222545-15-5) → (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene (210764-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

2: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

3: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

With sodium tetrahydroborate; cerium(III) chloride; pyridinium p-toluenesulfonate; methanesulfonyl chloride; In methanol; dichloromethane;

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

upstream raw materials:

3,4-dihydro-2H-pyran

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

p-methoxybenzyl chloride

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

Downstream raw materials:

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

(1R,2R,3S,4S)-2-<(1R)-1-methylprop-2-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-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

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