4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

Base Information

Chemical Name:4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose
CAS No.:956485-09-9
Molecular Formula:C₃₆H₄₂O₆Si
Molecular Weight:598.811
Hs Code.:

Synonyms:4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

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Chemical Property of 4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

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Technology Process of 4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

There total 15 articles about 4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose 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: 64.0%

: 956485-07-7
((3aR,6S,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxole-5,5-diyl)dimethanol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 956485-09-9
4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

: 956485-08-8
((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Guidance literature:: ((3aR,6S,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxole-5,5-diyl)dimethanol; tert-butylchlorodiphenylsilane; With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h;

With methanol; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

: 939-26-4
2-bromomethylnaphthyl bromide

: 956485-09-9
4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

: 956485-08-8
((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice

2.1: acetic acid / water / 16 h / 20 °C

3.1: sodium periodate / 1,4-dioxane; water / 1 h

4.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / Cooling with ice

5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

5.2: 2 h / 20 °C

With sodium periodate; sodium hydride; acetic acid; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

: 1057385-93-9
(3aR,5S,6R,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde

: 956485-09-9
4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

: 956485-08-8
((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / Cooling with ice

2.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

2.2: 2 h / 20 °C

With triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;