(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS No.: 115693-78-2
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• DSSTox Substance ID: DTXSID501133291
• Nikkaji Number: J3.255.950F
• Mol file: 115693-78-2.mol

Synonyms:DTXSID501133291;115693-78-2;3-O-[(4-Methoxyphenyl)methyl]-1,2:5,6-bis-O-(1-methylethylidene)-alpha-D-allofuranose

Chemical Property of (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 380.18350323
• Heavy Atom Count: 27
• Complexity: 515

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OCC4=CC=C(C=C4)OC)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@@H]2[C@H]([C@@H]3[C@H](O2)OC(O3)(C)C)OCC4=CC=C(C=C4)OC)C

Technology Process of (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

There total 16 articles about (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[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%

2-(4-methoxybenzyloxy)-4-methylquinoline (937184-70-8) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,4-dimethylquinolin-2(1H)-one (2584-47-6) + 1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose (115693-78-2,142226-15-1,69940-02-9)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1055/s-2008-1032132

Reference yield: 95.0%

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) + p-methoxybenzyl chloride (824-94-2) → 3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (69940-02-9,142226-15-1,115693-78-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1055/s-1997-1003

Reference yield: 92.0%

p-methoxybenzyl chloride (824-94-2) + Diacetone D-glucose (2595-05-3) → 3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (69940-02-9,142226-15-1,115693-78-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1271/bbb.63.736

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

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

2-[(4-methoxybenzyl)oxy]-3-nitropyridine

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

Downstream raw materials:

1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

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

4-methoxy-benzaldehyde

3-O-Acetyl-4-[(1R,4R,2E)-4-benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose