(3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 329899-60-7
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• Mol file: 329899-60-7.mol

Synonyms:(3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 1 articles about (3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-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: 100.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (329899-64-1) + p-methoxybenzyl chloride (824-94-2) → (3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (329899-60-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/S0040-4039(00)95485-6

Reference yield: 94.0%

(3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (329899-60-7) → 1-[(3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol (69940-04-1,109536-51-8,142226-16-2)

Guidance literature:

With sulfuric acid; In methanol; Ambient temperature;

DOI:10.1016/S0040-4039(00)95485-6

Reference yield:

(3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (329899-60-7) → (4R,5R)-1-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-4,6-isopropylidenedioxy-5-(4-methoxybenzyloxy)hexan-1-one (113981-32-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / 2percent-H₂SO₄ / methanol / Ambient temperature

2: NaIO₄ / methanol; H₂O / Ambient temperature

3: NaBH₄

4: 82 percent / NaH / dimethylsulfoxide; tetrahydrofuran

6: 87 percent / Raney Ni (W-2) / ethanol / Ambient temperature

7: 100 percent / (COCl)2, Et₃N / CH₂Cl₂; dimethylsulfoxide

8: 1.) NaH; 2.) H₂ / 2.) Pd-C / 1.) DMSO-THF, 0 deg C; 2.) AcOEt

With sodium tetrahydroborate; sodium periodate; oxalyl dichloride; Raney Ni (W-2); sulfuric acid; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)95485-6

upstream raw materials:

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

p-methoxybenzyl chloride

Downstream raw materials:

1-[(3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol

(2R,3R)-2,4-isopropylidenedioxy-3-(4-methoxybenzyloxy)butanal

[(3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

(3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde