(3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol
• CAS No.: 97834-06-5
• Molecular Formula: C₁₃H₂₂O₆
• Molecular Weight: 274.314
• Mol file: 97834-06-5.mol

Synonyms:(3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol

Chemical Property of (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol

There total 7 articles about (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol 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: 82.0%

Diacetone D-glucose (2595-05-3) + methyl iodide (74-88-4) → 5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl methyl ether (29587-01-7,32087-37-9,43138-64-3,65725-73-7,97834-06-5,18968-49-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃;

DOI:10.2174/157017811797249290

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl methyl ether (29587-01-7,32087-37-9,43138-64-3,65725-73-7,97834-06-5,18968-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.49 g / NaBH₄ / methanol

2: NaH / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jo070520d

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl methyl ether (29587-01-7,32087-37-9,43138-64-3,65725-73-7,97834-06-5,18968-49-5)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂

2: 1.35 g / sodium borohydride / ethanol; H₂O

3: 1.) 60percent sodium hydride / 1.) DMSO, room temp., 1 h, 2.) DMSO, room temp., 2 h

With sodium tetrahydroborate; 3 A molecular sieve; sodium hydride; pyridinium chlorochromate; In ethanol; dichloromethane; water;

DOI:10.1248/cpb.35.2894

upstream raw materials:

(1,2:5,6)-di-O-isopropylidene-D-gulose

methyl iodide

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

Downstream raw materials:

(3R,4R,5R,6R)-6-Hydroxymethyl-4-methoxy-tetrahydro-pyran-2,3,5-triol

C₂₆H₃₅O₅SiN₃

6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-α-D-allofuranose

6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose