5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

Base Information

• Chemical Name: 5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS No.: 460052-80-6
• Molecular Formula: C₂₈H₃₄O₆Si
• Molecular Weight: 494.66

Synonyms:5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

Chemical Property of 5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

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Technology Process of 5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

There total 2 articles about 5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol 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: 57.0%

furan (110-00-9) + 5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose (103763-15-1) → 5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol (460052-80-6)

Guidance literature:

furan; With n-butyllithium; In tetrahydrofuran; hexane; at -40 ℃; for 1h;

5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose; In tetrahydrofuran; hexane; at -40 - 20 ℃;

DOI:10.1016/S0040-4020(02)00319-8

Reference yield:

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0) → 5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol (460052-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 75 percent / pyridinium dichromate / (CH₃CO)2O / CH₂Cl₂ / 3 h / Heating

2.1: n-C₄H₉Li / tetrahydrofuran; hexane / 1 h / -40 °C

2.2: 57 percent / tetrahydrofuran; hexane / -40 - 20 °C

With dipyridinium dichromate; n-butyllithium; acetic anhydride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0040-4020(02)00319-8

Reference yield: 85.0%

5-t-butyldiphenylsilyloxymethyl-6-(2-furyl)-2,2-dimethyl-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol (460052-80-6) → C28H34O7Si (460052-84-0)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; water; at -5 ℃;

DOI:10.1016/S0040-4020(02)00319-8

upstream raw materials:

furan

5-O-tert-butyldiphenylsilyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose-3-ulose

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

C₂₈H₃₄O₇Si

C₂₉H₃₈O₇Si

C₂₉H₃₈O₇Si

5-t-butyldiphenylsiloxymethyl-6'-methoxy-2,2-dimethyl-(3'R,3aR,5S,6R,6'S,6aR)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate

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