(1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

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Chemical Name:(1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane
CAS No.:184964-77-0
Molecular Formula:C₂₁H₂₆Cl₃NO₅
Molecular Weight:478.8
Hs Code.:

Synonyms:(1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

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Chemical Property of (1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

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Technology Process of (1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

There total 8 articles about (1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane 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:

: 184964-75-8
2,2,2-Trichloro-acetimidic acid (E)-4-benzyloxy-3-((3aR,5S,6R,6aR)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-2-enyl ester

: 184964-77-0
(1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Guidance literature:: In toluene; at 150 ℃; for 89h; Yield given;
DOI:10.1039/c39950000793

Reference yield:

: 26291-75-8,81114-49-0,109200-09-1,128461-80-3
(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

: 184964-77-0
(1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 6 steps

1.1: di-n-butyltin oxide / toluene / 3 h / Heating

1.2: 66 percent / cesium fluoride / dimethylformamide / 18 h / 20 °C

2.1: CrO₃; aq. sulfuric acid / acetone / 1 h / 0 °C

3.1: toluene / 16 h / 20 - 60 °C

4.1: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -15 °C

5.1: NaH / diethyl ether / 0.25 h / -15 - 20 °C

5.2: diethyl ether / 2.3 h / -15 - 20 °C

6.1: 160 mg / toluene / 89 h / 140 °C

With chromium(VI) oxide; sulfuric acid; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; In diethyl ether; dichloromethane; acetone; toluene; 1.1: stannylation / 1.2: Alkylation / 2.1: Jones oxidation / 3.1: Wittig reaction / 4.1: Reduction / 5.1: Metallation / 5.2: Addition / 6.1: Overman rearrangement;
DOI:10.1016/S0040-4020(97)01015-6

Reference yield:

: 114144-67-1
6-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-allofuranose

: 184964-77-0
(1R,3S,4R,5R)-3-[(1RS)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 5 steps

1.1: CrO₃; aq. sulfuric acid / acetone / 1 h / 0 °C

2.1: toluene / 16 h / 20 - 60 °C

3.1: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -15 °C

4.1: NaH / diethyl ether / 0.25 h / -15 - 20 °C

4.2: diethyl ether / 2.3 h / -15 - 20 °C

5.1: 160 mg / toluene / 89 h / 140 °C

With chromium(VI) oxide; sulfuric acid; sodium hydride; diisobutylaluminium hydride; In diethyl ether; dichloromethane; acetone; toluene; 1.1: Jones oxidation / 2.1: Wittig reaction / 3.1: Reduction / 4.1: Metallation / 4.2: Addition / 5.1: Overman rearrangement;
DOI:10.1016/S0040-4020(97)01015-6