1,3-Dioxolo4,5-cpyridin-7-ol, 4-(1,1-dimethylethyl)dimethylsilyloxymethylhexahydro-2,2-dimethyl-, 3aS-(3a.alpha.,4.beta.,7.alpha.,7a.alpha.)-

Base Information

• Chemical Name: 1,3-Dioxolo4,5-cpyridin-7-ol, 4-(1,1-dimethylethyl)dimethylsilyloxymethylhexahydro-2,2-dimethyl-, 3aS-(3a.alpha.,4.beta.,7.alpha.,7a.alpha.)-
• CAS No.: 151252-21-0
• Molecular Formula: C₁₅H₃₁NO₄Si
• Molecular Weight: 317.501
• Mol file: 151252-21-0.mol

Synonyms:1,3-Dioxolo[4,5-c]pyridin-7-ol,4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-2,2-dimethyl-,[3aS-(3aa,4b,7a,7aa)]- (9CI)

Chemical Property of 1,3-Dioxolo4,5-cpyridin-7-ol, 4-(1,1-dimethylethyl)dimethylsilyloxymethylhexahydro-2,2-dimethyl-, 3aS-(3a.alpha.,4.beta.,7.alpha.,7a.alpha.)-

Chemical Property:

• Boiling Point: 398.2±42.0 °C(Predicted)
• PKA: 13.75±0.60(Predicted)
• PSA: 59.95000
• Density: 1.003±0.06 g/cm3(Predicted)
• LogP: 2.18980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3-Dioxolo4,5-cpyridin-7-ol, 4-(1,1-dimethylethyl)dimethylsilyloxymethylhexahydro-2,2-dimethyl-, 3aS-(3a.alpha.,4.beta.,7.alpha.,7a.alpha.)-

There total 8 articles about 1,3-Dioxolo4,5-cpyridin-7-ol, 4-(1,1-dimethylethyl)dimethylsilyloxymethylhexahydro-2,2-dimethyl-, 3aS-(3a.alpha.,4.beta.,7.alpha.,7a.alpha.)- 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:

(3aR,6S,6aR)-6-Azidomethyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol → (3aS,4R,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol (151252-21-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; Yield given;

DOI:10.1016/S0040-4039(00)73649-5

Reference yield:

11,2:4,6-di-O-isopropylidene-α-L-sorbofuranose (18604-19-8,62133-03-3) → (3aS,4R,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol (151252-21-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Me₂SO, (CF₃CO)2O, Et₃N, 2.) NaBH₄ / 1.) CH₂Cl₂, 2.) EtOH

2: 85 percent / camphersulfonic acid / acetone

3: Et₃N / CH₂Cl₂

4: NaN₃ / dimethylsulfoxide / 80 °C

5: BF₃*OEt₂ / 0 °C

6: MeONa / methanol

7: imidazole / dimethylformamide

8: H₂ / Pd-C / ethanol

With 1H-imidazole; sodium tetrahydroborate; sodium azide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; sodium methylate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)73649-5

Reference yield:

1,2:3,4-Di-O-isopropylidene-α-L-tagatofuranose (151377-80-9) → (3aS,4R,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol (151252-21-0)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂

2: NaN₃ / dimethylsulfoxide / 80 °C

3: BF₃*OEt₂ / 0 °C

4: MeONa / methanol

5: imidazole / dimethylformamide

6: H₂ / Pd-C / ethanol

With 1H-imidazole; sodium azide; boron trifluoride diethyl etherate; hydrogen; sodium methylate; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)73649-5

upstream raw materials:

11,2:4,6-di-O-isopropylidene-α-L-sorbofuranose

1,2:3,4-Di-O-isopropylidene-α-L-tagatofuranose

(3aR,6S,6aR)-6-Azidomethyl-4-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

6-Azido-6-deoxy-1,2:3,4-di-O-isopropylidene-α-L-tagatose

Refernces