(3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone

Base Information

Chemical Name:(3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone
CAS No.:199734-91-3
Molecular Formula:C₂₁H₃₃NO₃Si
Molecular Weight:375.583
Hs Code.:

Synonyms:(3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone

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Chemical Property of (3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone

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Technology Process of (3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone

There total 13 articles about (3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone 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: 92.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 166541-05-5
(3R,4S,5R)-5-benzyloxymethyl-4-hydroxy-3-methyl-5-vinyl-2-pyrrolidinone

: 199734-91-3
(3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 43h;
DOI:10.1016/S0040-4020(97)01015-6

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

: 199734-91-3
(3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 11 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

9.1: Jones reagent / acetone / 22 h / 0 - 5 °C

10.1: 1.34 g / NaBH₄ / methanol / 3 h / 0 - 20 °C

11.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 43 h / 0 - 20 °C

With 2,6-dimethylpyridine; chromium(VI) oxide; sodium tetrahydroborate; sodium periodate; jones reagent; 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 / 9.1: Jones oxidation / 10.1: Reduction / 11.1: silylation;
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

: 199734-91-3
(3R,4S,5R)-5-benzyloxymethyl-4-(tert-butyldimethylsilyl)oxy-3-methyl-5-vinyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 10 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

8.1: Jones reagent / acetone / 22 h / 0 - 5 °C

9.1: 1.34 g / NaBH₄ / methanol / 3 h / 0 - 20 °C

10.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 43 h / 0 - 20 °C

With 2,6-dimethylpyridine; chromium(VI) oxide; sodium tetrahydroborate; sodium periodate; jones reagent; 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 / 8.1: Jones oxidation / 9.1: Reduction / 10.1: silylation;
DOI:10.1016/S0040-4020(97)01015-6