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

Base Information

Chemical Name:5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate
CAS No.:460052-90-8
Molecular Formula:C₃₁H₄₀O₈Si
Molecular Weight:568.739
Hs Code.:

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

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Chemical Property of 5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate

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Technology Process of 5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate

There total 6 articles about 5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate 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: 87.0%

: 108-24-7
acetic anhydride

: 460052-89-5
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-ol

: 460052-90-8
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1016/S0040-4020(02)00319-8

Reference yield:

: 172751-32-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

: 460052-90-8
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 65 percent / tetrahydrofuran; hexane / -40 - 20 °C

2.1: 85 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 0.08 h / -5 °C

3.1: 33 percent / Ag₂O / CH₂Cl₂ / 12 h / 20 °C

4.1: 76 percent / NaBH₄ / CeCl₃*7H₂O / methanol / 0 °C

5.1: 87 percent / (C₂H₅)3N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; triethylamine; silver(l) oxide; cerium(III) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(02)00319-8

Reference yield:

: 114738-04-4
(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

: 460052-90-8
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3'S,3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-yl acetate

Guidance literature:: Multi-step reaction with 6 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: 65 percent / tetrahydrofuran; hexane / -40 - 20 °C

3.1: 85 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 0.08 h / -5 °C

4.1: 33 percent / Ag₂O / CH₂Cl₂ / 12 h / 20 °C

5.1: 76 percent / NaBH₄ / CeCl₃*7H₂O / methanol / 0 °C

6.1: 87 percent / (C₂H₅)3N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; triethylamine; silver(l) oxide; cerium(III) chloride; acetic anhydride; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(02)00319-8