(3aS,4S,6aR)-5-(tert-butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid

Base Information

• Chemical Name: (3aS,4S,6aR)-5-(tert-butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid
• CAS No.: 127910-62-7
• Molecular Formula: C₁₃H₂₁NO₆
• Molecular Weight: 287.313
• DSSTox Substance ID: DTXSID501103355
• Mol file: 127910-62-7.mol

Synonyms:127910-62-7;(3aS,4S,6aR)-5-(tert-butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid;(3As,4S,6aR)-2,2-dimethyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid;5H-1,3-Dioxolo[4,5-c]pyrrole-4,5-dicarboxylic acid,tetrahydro-2,2-dimethyl-, 5-(1,1-dimethylethyl) ester,[3aS-(3aa,4b,6aa)]-;SCHEMBL24686938;DTXSID501103355;PS-2004;F70935;(3aS,4S,6aR)-5-[(tert-butoxy)carbonyl]-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid;5H-1,3-Dioxolo[4,5-c]pyrrole-4,5-dicarboxylic acid, tetrahydro-2,2-dimethyl-, 5-(1,1-dimethylethyl) ester, [3aS-(3aalpha,4beta,6aalpha)]-

Chemical Property of (3aS,4S,6aR)-5-(tert-butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid

Chemical Property:

• PSA: 85.30000
• LogP: 1.14830
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 287.13688739
• Heavy Atom Count: 20
• Complexity: 427

Purity/Quality:

(3AS,4S,6aR)-5-(tert-Butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid >97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2CN(C(C2O1)C(=O)O)C(=O)OC(C)(C)C)C
• Isomeric SMILES: CC1(O[C@@H]2CN([C@@H]([C@@H]2O1)C(=O)O)C(=O)OC(C)(C)C)C

Technology Process of (3aS,4S,6aR)-5-(tert-butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid

There total 9 articles about (3aS,4S,6aR)-5-(tert-butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid 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: 71.0%

(1R,5S,6S)-tert-butyl 6-formyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane-7-carboxylate (127910-61-6) → 7-tert-butyl 6-hydrogen (1R,5S,6S)-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane-6,7-dicarboxylate (127910-62-7)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile;

DOI:10.1039/c39900000051

Reference yield:

2,3-O-isopropylidene-D-erythrose (189996-60-9) → 7-tert-butyl 6-hydrogen (1R,5S,6S)-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane-6,7-dicarboxylate (127910-62-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) butyllithium / 1) THF, hexanes, -60 to 0 deg C, 2) THF, -78 deg C to room temperature

2: 1) diethyl azodicarboxylate, triphenylphosphine, 2) diphenylphosphoryl azide / 1) THF, 0 deg C, 2) THF, 0 deg C, 1 h

3: 2) sodium borohydride / 1) n-octane, reflux, 4 h, 2) methanol, ice cooling, 30 min

4: 91 percent / triethylamine / CH₂Cl₂ / 12 h

5: 93 percent / thallium(III) trifluoroacetate / diethyl ether; H₂O / 12 h / Ambient temperature

6: 71 percent / sodium periodate, ruthenium trichloride / H₂O; CCl₄; acetonitrile / 6 h

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; n-butyllithium; diphenylphosphoranyl azide; triethylamine; triphenylphosphine; diethylazodicarboxylate; thallium(III) trifluoroacetate; In tetrachloromethane; diethyl ether; dichloromethane; water; acetonitrile;

Reference yield:

(4S,5R)-4-(1,3-dithian-2-ylidenemethyl)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (127811-88-5) → 7-tert-butyl 6-hydrogen (1R,5S,6S)-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane-6,7-dicarboxylate (127910-62-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) diethyl azodicarboxylate, triphenylphosphine, 2) diphenylphosphoryl azide / 1) THF, 0 deg C, 2) THF, 0 deg C, 1 h

2: 2) sodium borohydride / 1) n-octane, reflux, 4 h, 2) methanol, ice cooling, 30 min

3: 91 percent / triethylamine / CH₂Cl₂ / 12 h

4: 93 percent / thallium(III) trifluoroacetate / diethyl ether; H₂O / 12 h / Ambient temperature

5: 71 percent / sodium periodate, ruthenium trichloride / H₂O; CCl₄; acetonitrile / 6 h

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; diphenylphosphoranyl azide; triethylamine; triphenylphosphine; diethylazodicarboxylate; thallium(III) trifluoroacetate; In tetrachloromethane; diethyl ether; dichloromethane; water; acetonitrile;

upstream raw materials:

(1R,5S,6S)-tert-butyl 6-formyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane-7-carboxylate

2,3-O-isopropylidene-D-erythrose

di-tert-butyl dicarbonate

(1R,5S,6S)-6-(1,3-dithian-2-yl)-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane

Downstream raw materials:

(2S,3S,4R)-3,4-dihydroxy-L-proline

(2S,3S,4R)-3,4-dihydroxyproline trifluoroacetic acid salt

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