(3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Base Information

• Chemical Name: (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
• CAS No.: 211623-13-1
• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.422
• Mol file: 211623-13-1.mol

Synonyms:(3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Chemical Property of (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

There total 6 articles about (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 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: 71.0%

(3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol → (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (211623-13-1)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00080-9

Reference yield: 61.0%

(1R)-1-[(2R,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-yl]ethanol + benzyl bromide (100-39-0) + (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (70147-48-7) → (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (211623-13-1)

Guidance literature:

In N,N-dimethyl-formamide;

Reference yield:

2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannose (91738-34-0,91738-35-1) → (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (211623-13-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO; 2.) tetrabutylammonium bromide / 1.) toluene, reflux, 16 h; 2.) toluene, 80 deg C, 1 h

2: 71 percent / pyridinium chlorochromate, 4 Angstroem mol. sieves / CH₂Cl₂ / 2 h / Ambient temperature

With 4 A molecular sieve; tetrabutylammomium bromide; di(n-butyl)tin oxide; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0008-6215(98)00080-9

upstream raw materials:

2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannose

benzyl bromide

(3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

Downstream raw materials:

(3S,4R,5S)-3-Benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-dihydro-furan-2-one