(1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one

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Chemical Name:(1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one
CAS No.:795308-15-5
Molecular Formula:C₂₂H₂₉IO₈
Molecular Weight:548.372
Hs Code.:

Synonyms:(1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one

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Chemical Property of (1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one

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Technology Process of (1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one

There total 3 articles about (1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-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: 82.0%

: 795308-14-4
(1'R,3S,3aS,7aR)-3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-7a-[(4-methoxybenzyl)oxy]-3-methyl-3a,6,7,7a-tetrahydro-2-benzofuran-1(3H)-one

: 795308-15-5
(1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 4h;
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

: 795308-15-5
(1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one

Guidance literature:: Multi-step reaction with 3 steps

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

2: 78 percent / N-iodosuccinimide / tetrahydrofuran / 2 h

3: 82 percent / NMO; MeSO₂NH₂; osmium tetroxide / 2-methyl-propan-2-ol; H₂O / 4 h / 0 °C

With N-iodo-succinimide; osmium(VIII) oxide; N-methyl-2-indolinone; methanesulfonamide; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; 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

: 795308-15-5
(1'R,3S,4S,5R,3aS,7aR) 3-[2'-(1,3-dioxolan-2-yl)-1'-iodoethyl]-4,5-dihydroxy-7a-[(4-methoxybenzyl)oxy]-3-methylhexahydro-2-benzofuran-1(3H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / N-iodosuccinimide / tetrahydrofuran / 2 h

2: 82 percent / NMO; MeSO₂NH₂; osmium tetroxide / 2-methyl-propan-2-ol; H₂O / 4 h / 0 °C

With N-iodo-succinimide; osmium(VIII) oxide; N-methyl-2-indolinone; methanesulfonamide; In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.1002/ejoc.200400262