methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside

Base Information

Chemical Name:methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside
CAS No.:866885-26-9
Molecular Formula:C₄₂H₅₂O₉Si
Molecular Weight:728.955
Hs Code.:

Synonyms:methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside

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Chemical Property of methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside

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Technology Process of methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside

There total 19 articles about methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside 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: 86.0%

: 866885-23-6
methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

: 3282-30-2
pivaloyl chloride

: 866885-26-9
methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1081/CAR-200067008

Reference yield:

: 866885-19-0
dimethyl(2-naphthylmethyl)vinylsilane

: 866885-26-9
methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C

1.2: 58 percent / hydrogen peroxide; sodium hydroxide / ethanol; H₂O / 1 h / Heating

2.1: 63 percent / diethyl ether; toluene / 2.5 h / -15 - 20 °C

3.1: 98 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / 20 °C

4.1: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

5.1: 0.683 g / CH₂Cl₂ / 15 h / 20 °C

6.1: 86 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

With dmap; 3,3-dimethyldioxirane; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;
DOI:10.1081/CAR-200067008

Reference yield:

: 866885-20-3
2-[dimethyl(2-naphthylmethyl)silyl]ethanol

: 866885-26-9
methyl 3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-2-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 63 percent / diethyl ether; toluene / 2.5 h / -15 - 20 °C

2: 98 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / 20 °C

3: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

4: 0.683 g / CH₂Cl₂ / 15 h / 20 °C

5: 86 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

With dmap; 3,3-dimethyldioxirane; In diethyl ether; dichloromethane; acetone; toluene;
DOI:10.1081/CAR-200067008