(1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

Base Information

Chemical Name:(1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate
CAS No.:352670-32-7
Molecular Formula:C₂₃H₂₈Cl₃NO₉
Molecular Weight:568.836
Hs Code.:

Synonyms:(1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

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Chemical Property of (1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

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Technology Process of (1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

There total 25 articles about (1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate 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: 88.0%

: 1421851-07-1
(1R)-1-((1R,2S,3S,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-(2,2,2-trichloroacetamido)-7-oxabicyclo[4.1.0]heptan-3-yl)prop-2-yn-1-yl acetate

: 352670-32-7
(1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

Guidance literature:: With potassium permanganate; sodium periodate; sodium hydrogencarbonate; In water; tert-butyl alcohol; at 20 ℃; for 0.5h;
DOI:10.1021/jo302773f

Reference yield:

: Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-formyl-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester

: 149-73-5
trimethyl orthoformate

: 352670-32-7
(1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 20 ℃; for 10h;
DOI:10.1002/(SICI)1521-3773(19991018)38:20<3081::AID-ANIE3081>3.0.CO;2-6

Reference yield:

: 271256-59-8
2,2,2-Trichloro-N-[(1R,6S)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-oxo-1-vinyl-cyclohex-3-enyl]-acetamide

: 352670-32-7
(1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 71 percent / NaBH₄; CeCl₃*7H₂O / ethanol; CH₂Cl₂ / 2.5 h / 0 - 20 °C

2.1: 95 percent / m-chloroperbenzoic acid; Na₂HPO₄ / CH₂Cl₂ / 24 h / 20 °C

3.1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 22 h / 20 °C

4.1: O₃ / methanol / 1.17 h / -78 °C

4.2: 96 percent / Me₂S / methanol / -78 - 20 °C

5.1: EtMgBr / tetrahydrofuran; diethyl ether / 0.58 h / 0 - 20 °C

5.2: tetrahydrofuran; diethyl ether / 2 h / 20 °C

6.1: n-Bu₄NF / tetrahydrofuran / 2.5 h / 20 °C

7.1: 7.37 g / pyridine / 5.5 h

8.1: 75 percent / RuO₂(H₂O)x; NaIO₄ / acetonitrile; CCl₄; H₂O / 4.5 h / 20 °C

9.1: H₅IO₆ / ethyl acetate / 24 h / 20 °C

10.1: 772 mg / DL-camphorsulfonic acid / methanol / 10 h / 20 °C

With ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; cerium(III) chloride; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; ozone; periodic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)00382-9