(3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Base Information

• Chemical Name: (3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole
• CAS No.: 191275-96-4
• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.439
• Mol file: 191275-96-4.mol

Synonyms:(3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Chemical Property of (3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

There total 1 articles about (3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 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: 70.0%

benzyl bromide (100-39-0) + 2,3:5,6-di-O-isopropylidene-1-C-methyl-β-D-mannofuranose (72926-55-7) → (3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole (191275-96-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00189-3

Reference yield:

(3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole (191275-96-4) → (2S,3R,4S,5R)-2-Methyl-1-[2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-piperidine-3,4,5-triol

Guidance literature:

Multi-step reaction with 7 steps

1: periodic acid / tetrahydrofuran; H₂O

2: NaBH₄ / methanol

3: pyridine / CH₂Cl₂

4: NaN₃ / dimethylformamide / 0 °C

5: 74 percent / ammonium formate / 10percent Pd-C / 60 °C

6: 26 percent / 45 °C

7: 1.) DBU, 2.) TFA / 1.) MeOH, 2.) H₂O

With pyridine; sodium tetrahydroborate; sodium azide; ammonium formate; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00189-3

Reference yield:

(3aS,4R,6R,6aS)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole (191275-96-4) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[2-((3aR,4S,7R,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-ylmethyl)-phenoxy]-tetrahydro-pyran-3-yl ester (191276-05-8)

Guidance literature:

Multi-step reaction with 6 steps

1: periodic acid / tetrahydrofuran; H₂O

2: NaBH₄ / methanol

3: pyridine / CH₂Cl₂

4: NaN₃ / dimethylformamide / 0 °C

5: 74 percent / ammonium formate / 10percent Pd-C / 60 °C

6: 26 percent / 45 °C

With pyridine; sodium tetrahydroborate; sodium azide; ammonium formate; periodic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00189-3

upstream raw materials:

benzyl bromide

2,3:5,6-di-O-isopropylidene-1-C-methyl-β-D-mannofuranose

Downstream raw materials:

((3aS,4R,6R,6aS)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol

(3aS,4R,6R,6aS)-6-Azidomethyl-4-benzyloxy-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[2-((3aR,4S,7R,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-ylmethyl)-phenoxy]-tetrahydro-pyran-3-yl ester

(3aR,4S,7R,7aS)-2,2,4-Trimethyl-5-[3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propyl]-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol