Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester

Base Information

Chemical Name:Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester
CAS No.:184964-82-7
Molecular Formula:C₁₈H₂₀Cl₃NO₅
Molecular Weight:436.719
Hs Code.:

Synonyms:Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester

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Chemical Property of Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester

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Technology Process of Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester

There total 10 articles about Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester 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:

: (2RS,3R,4R,5S)-5-[(1R)-1-benzyloxymethyl-1-trichloroacetylamino-2-propenyl]-2,3-dihydroxy-4-methyltetrahydrofuran

: 184964-82-7
Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester

Guidance literature:: With sodium periodate; In methanol; water; Ambient temperature;
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

: 184964-82-7
Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester

Guidance literature:: Multi-step reaction with 8 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

7.1: 72 percent / trifluoroacetic acid / H₂O / 5 h / 0 °C

8.1: sodium periodate / methanol; H₂O / 28 h / 0 - 20 °C

With chromium(VI) oxide; sodium periodate; sulfuric acid; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; water; 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 / 7.1: Hydrolysis / 8.1: Oxidation;
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

: 184964-82-7
Formic acid (2R,3S,4R)-2-benzyloxymethyl-5-hydroxy-4-methyl-1-(2,2,2-trichloro-acetyl)-2-vinyl-pyrrolidin-3-yl ester

Guidance literature:: Multi-step reaction with 7 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

6.1: 72 percent / trifluoroacetic acid / H₂O / 5 h / 0 °C

7.1: sodium periodate / methanol; H₂O / 28 h / 0 - 20 °C

With chromium(VI) oxide; sodium periodate; sulfuric acid; sodium hydride; diisobutylaluminium hydride; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; 1.1: Jones oxidation / 2.1: Wittig reaction / 3.1: Reduction / 4.1: Metallation / 4.2: Addition / 5.1: Overman rearrangement / 6.1: Hydrolysis / 7.1: Oxidation;
DOI:10.1016/S0040-4020(97)01015-6