1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate

Base Information

Chemical Name:1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate
CAS No.:284490-14-8
Molecular Formula:C22H38N2O6Si
Molecular Weight:454.639
Hs Code.:
DSSTox Substance ID:DTXSID601098727
Mol file:284490-14-8.mol

1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate

Synonyms:SCHEMBL15718936;JXRVZIDPWUDVAH-XHCSWFMASA-N;DTXSID601098727;1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate;284490-14-8

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Chemical Property of 1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate

Chemical Property:

PSA：101.25000
LogP:4.41958
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:7
Exact Mass:454.24991347
Heavy Atom Count:31
Complexity:771

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1(OC2C(N(C(C2O1)C(=CO)C#N)C(=O)OC(C)(C)C)CO[Si](C)(C)C(C)(C)C)C
Isomeric SMILES:CC1(O[C@@H]2[C@H](N([C@H]([C@@H]2O1)/C(=C/O)/C#N)C(=O)OC(C)(C)C)CO[Si](C)(C)C(C)(C)C)C

Technology Process of 1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate

There total 7 articles about 1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate 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:

: 4-(tert-butyl-dimethyl-silanyloxymethyl)-6-(1-cyano-2-dimethylamino-vinyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

: 284490-14-8
(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: With acetic acid; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

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

: 284490-14-8
(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / CH₂Cl₂ / 16 h / 20 °C

2: dimethylformamide / 1 h / 65 - 70 °C

3: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

With acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Condensation / 3: Hydrolysis;
DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

: 153172-31-7
(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

: 284490-14-8
(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: Multi-step reaction with 5 steps

1.1: NCS / pentane / 1 h

1.2: LiTMP / tetrahydrofuran / -78 °C

2.1: 0.83 g / tetrahydrofuran / 1 h / -78 °C

3.1: 85 percent / CH₂Cl₂ / 16 h / 20 °C

4.1: dimethylformamide / 1 h / 65 - 70 °C

5.1: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

With N-chloro-succinimide; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane; 1.1: Chlorination / 1.2: Elimination / 2.1: Addition / 3.1: Substitution / 4.1: Condensation / 5.1: Hydrolysis;
DOI:10.1016/S0040-4020(00)00194-0