(3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester
• CAS No.: 108861-55-8
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 108861-55-8.mol

Synonyms:

Chemical Property of (3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester

There total 13 articles about (3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester 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:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) → (3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester (108861-55-8)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridinium chlorochromate / CH₂Cl₂ / 20 °C

2: benzene / Heating

3: H₂ / Pd / methanol

4: LiAlH₄ / tetrahydrofuran

5: pyridine / 0 °C

6: NaN₃ / dimethylformamide / 40 °C

7: 90 percent / acetic acid, H₂O / methanol / 40 °C

8: 1.) NaIO₄, 2.) H₂ / 2.) palladium black / 1.) MeOH, H₂O, 2.) AcOH

9: NaHCO₃ / diethyl ether; H₂O / 20 °C

With pyridine; sodium periodate; lithium aluminium tetrahydride; sodium azide; water; hydrogen; sodium hydrogencarbonate; acetic acid; pyridinium chlorochromate; palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)84715-2

Reference yield:

1-[(3aR,5S,6R,6aR)-2,2-Dimethyl-6-(2-triazirin-1-yl-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol → (3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester (108861-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaIO₄, 2.) H₂ / 2.) palladium black / 1.) MeOH, H₂O, 2.) AcOH

2: NaHCO₃ / diethyl ether; H₂O / 20 °C

With sodium periodate; hydrogen; sodium hydrogencarbonate; palladium; In diethyl ether; water;

DOI:10.1016/S0040-4039(00)84715-2

Reference yield:

[(3aR,5S,6R,6aR)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid methyl ester (18427-18-4,36807-87-1,58787-84-1,58787-86-3) → (3aR,4aS,8aR,8bR)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyridine-6-carboxylic acid benzyl ester (108861-55-8)

Guidance literature:

Multi-step reaction with 6 steps

1: LiAlH₄ / tetrahydrofuran

2: pyridine / 0 °C

3: NaN₃ / dimethylformamide / 40 °C

4: 90 percent / acetic acid, H₂O / methanol / 40 °C

5: 1.) NaIO₄, 2.) H₂ / 2.) palladium black / 1.) MeOH, H₂O, 2.) AcOH

6: NaHCO₃ / diethyl ether; H₂O / 20 °C

With pyridine; sodium periodate; lithium aluminium tetrahydride; sodium azide; water; hydrogen; sodium hydrogencarbonate; acetic acid; palladium; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84715-2

upstream raw materials:

benzyl chloroformate

Methanesulfonic acid (3aR,5S,6R,6aR)-6-(2-azido-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

[(3aR,5S,6R,6aR)-6-(2-Azido-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

(3R,3aS,7aS)-3-Hydroxy-2-methoxy-hexahydro-furo[2,3-c]pyridine-6-carboxylic acid benzyl ester

(3S,4R)-4-((R)-2,2-Bis-ethylsulfanyl-1-hydroxy-ethyl)-3-hydroxy-piperidine-1-carboxylic acid benzyl ester

(1S,3R,4R,5S)-3,5-Bis-benzyloxy-1-aza-bicyclo[2.2.2]octane

(3S,4R)-3-Benzyloxy-4-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester