5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-(1,3-dithian-2-yl)tetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6R,6aS)-

Base Information

Chemical Name:5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-(1,3-dithian-2-yl)tetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6R,6aS)-
CAS No.:258834-88-7
Molecular Formula:C₂₃H₄₃NO₅S₂Si
Molecular Weight:505.816
Hs Code.:

5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-(1,3-dithian-2-yl)tetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6R,6aS)-

Synonyms:5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-(1,3-dithian-2-yl)tetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6R,6aS)-

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Chemical Property of 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-(1,3-dithian-2-yl)tetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6R,6aS)-

Chemical Property:

PSA：107.83000
LogP:5.65030

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-(1,3-dithian-2-yl)tetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6R,6aS)-

There total 2 articles about 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-(1,3-dithian-2-yl)tetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6R,6aS)- 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: 94.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 258834-87-6
6-O-tert-butyldimethylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-allose propane-1,3-diyl dithioacetal

: 258834-88-7
N-tert-butoxycarbonyl-6-O-tert-butyldimethylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-allose propane-1,3-diyl dithioacetal

Guidance literature:: In dichloromethane; at 20 ℃; for 48h;
DOI:10.1016/S0968-0896(99)00210-2

Reference yield:

: 153172-33-9
(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

: 258834-88-7
N-tert-butoxycarbonyl-6-O-tert-butyldimethylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-allose propane-1,3-diyl dithioacetal

Guidance literature:: Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran / 0.5 h / -20 °C

1.2: 77 percent / 0.5 h / -78 °C

2.1: 94 percent / CH₂Cl₂ / 48 h / 20 °C

With n-butyllithium; In tetrahydrofuran; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Acylation;
DOI:10.1016/S0968-0896(99)00210-2

Reference yield:

: 258834-88-7
N-tert-butoxycarbonyl-6-O-tert-butyldimethylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-allose propane-1,3-diyl dithioacetal

: (2S,3S,4R,5R)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-pyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: CaCO₃; Hg(OTf)2 / acetonitrile; H₂O / 4 h

2: 0.194 g / NaBH₄ / ethanol / 1 h

3: iPr₂NEt / CH₂Cl₂ / 1 h

4: 0.054 g / K₂CO₃ / dimethylformamide / 6 h / 100 °C

5: 71 percent / TFA / H₂O / 16 h

With sodium tetrahydroborate; mercuric triflate; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; calcium carbonate; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Hydrolysis / 2: Reduction / 3: Substitution / 4: Substitution / 5: Hydrolysis;
DOI:10.1016/S0968-0896(99)00210-2