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

Base Information

Chemical Name:5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-one
CAS No.:460052-83-9
Molecular Formula:C₂₉H₃₆O₇Si
Molecular Weight:524.686
Hs Code.:

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

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

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

There total 4 articles about 5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-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: 36.0%

: 460052-81-7
C₂₈H₃₄O₇Si

: 74-88-4
methyl iodide

: 460052-82-8
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3aS,5R,6S,6'S,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-one

: 460052-83-9
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-one

Guidance literature:: With silver(l) oxide; In dichloromethane; at 20 ℃; for 12h;
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

: 460052-83-9
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-one

Guidance literature:: Multi-step reaction with 4 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

With N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; silver(l) oxide; acetic anhydride; In tetrahydrofuran; hexane; dichloromethane; water;
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

: 460052-83-9
5-t-butyldiphenylsilyloxymethyl-6'-methoxy-2,2-dimethyl-(3aS,5R,6S,6'R,6aS)-spiro[perhydrofuro[2,3-d][1,3]dioxole-6,2'-(3'H,6'H-pyran)]-3'-one

Guidance literature:: Multi-step reaction with 3 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

With N-Bromosuccinimide; n-butyllithium; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(02)00319-8