(1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

Base Information

Chemical Name:(1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one
CAS No.:117201-61-3
Molecular Formula:C₃₁H₃₈N₂O₉
Molecular Weight:582.651
Hs Code.:

(1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

Synonyms:(1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

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Chemical Property of (1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

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Technology Process of (1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

There total 6 articles about (1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-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: 93.0%

: 95237-55-1
(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

: 117201-61-3
(1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.1021/jo00261a009

Reference yield:

: 79243-92-8
(S)-(-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde

: 117201-61-3
(1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

Guidance literature:: Multi-step reaction with 2 steps

1: BuLi / tetrahydrofuran / -100 °C

2: 93 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/jo00261a009

Reference yield:

: 95237-56-2
(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

: 117201-61-3
(1S,6R,8S)-6-hydroxy-8-<(S)-1,2-dihydroxy-1,2-O-isopropylidene-2-methylethyl>-9-(p-methoxybenzyl)-1-<(p-methoxybenzyl)carbamoyl>-5-methylene-9-aza-2,5-dioxabicyclo<4.2.2>decan-10-one

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / PPTS / acetone / 12 h / Ambient temperature

2: 1.) NaH / 1.) DMF, 2.) 2 h

3: 80 percent / DDQ, H₂O / CH₂Cl₂ / 2 h / Ambient temperature

4: 93 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/jo00261a009