(3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole

Base Information

• Chemical Name: (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole
• CAS No.: 162808-23-3
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:(3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole

Chemical Property of (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole

Chemical Property:

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Technology Process of (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole

There total 12 articles about (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[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: 80.0%

(1R)-2,3-5,6-di-O-isopropylidene-1-C-phenyl-D-mannitol (138034-65-8) → (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole (162808-23-3)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1039/c39940001293

Reference yield: 24.0%

2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-mannofuranose → C-phenyl 2,3-O-isopropylidene-β-D-mannofuranoside (162808-24-4) + (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole (162808-23-3)

Guidance literature:

2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-mannofuranose; With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -40 ℃; for 1h; Inert atmosphere;

With potassium carbonate; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2012.08.023

Reference yield: 20.0%

2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-mannofuranoside (119842-22-7) → C-phenyl 2,3-O-isopropylidene-β-D-mannofuranoside (162808-24-4) + (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole (162808-23-3)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at -20 ℃; for 1h;

DOI:10.1016/S0040-4020(01)85344-8

upstream raw materials:

(1R)-2,3-5,6-di-O-isopropylidene-1-C-phenyl-D-mannitol

2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-mannofuranoside

O²,O³,O⁵,O⁶-diisopropylidene D-mannofuranose

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

Downstream raw materials:

Z-(C-phenyl 5,6-dideoxy-2-O-trifluoromethanesulphonyl-α-D-lyxo-heptofuranosi)uro-5-enono-3,7-lactone

(-)-7-epi-altholactone

(-) Altholactone

C-phenyl 2,3-O-isopropylidene-β-D-mannofuranoside

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