methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

Base Information

Chemical Name:methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate
CAS No.:795308-17-7
Molecular Formula:C₂₇H₃₆O₁₀
Molecular Weight:520.577
Hs Code.:

Synonyms:methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

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Chemical Property of methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

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Technology Process of methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

There total 3 articles about methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate 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: 86.0%

: 108-24-7
acetic anhydride

: 795308-18-8
methyl (1R,2S,3S,4R)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-3,4-dihydroxy-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

: 795308-17-7
methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

Guidance literature:: With dmap; In pyridine; for 2h;
DOI:10.1002/ejoc.200400262

Reference yield:

: 795308-12-2
(E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

: 795308-17-7
methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / Grubbs catalyst / toluene; CH₂Cl₂ / 2 h / 40 °C

2: 50 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; acetone / 48 h

3: 86 percent / DMAP / pyridine / 2 h

With dmap; AD-mix-α; methanesulfonamide; Grubbs catalyst first generation; In pyridine; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1002/ejoc.200400262

Reference yield:

: 795308-13-3
(1R,2R)-2-((E)-3-[1,3]Dioxolan-2-yl-1-methyl-propenyl)-1-(4-methoxy-benzyloxy)-cyclohex-3-enecarboxylic acid

: 795308-17-7
methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 50 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; acetone / 48 h

2: 86 percent / DMAP / pyridine / 2 h

With dmap; AD-mix-α; methanesulfonamide; In pyridine; water; acetone; tert-butyl alcohol;
DOI:10.1002/ejoc.200400262