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

Base Information

Chemical Name:5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose
CAS No.:1092803-37-6
Molecular Formula:C₃₇H₄₄O₆Si
Molecular Weight:612.838
Hs Code.:

Synonyms:5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

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Chemical Property of 5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

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Technology Process of 5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

There total 8 articles about 5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-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: 76.0%

: 1092803-01-4
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-vinyl-α-D-ribofuranose

: 1092803-37-6
5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

Guidance literature:: 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-vinyl-α-D-ribofuranose; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 24h;

With sodium perborate; In tetrahydrofuran; ethanol; water; at 50 ℃; for 4h;

Reference yield:

: C₄₅H₅₇BO₅Si

: 1092803-37-6
5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

Guidance literature:: With sodium perborate tetrahydrate; water; In tetrahydrofuran; ethanol; at 50 ℃; for 4h;
DOI:10.1021/ja105875e

Reference yield:

: 939-26-4
2-bromomethylnaphthyl bromide

: 1092803-37-6
5-O-(tert-butyldiphenylsilyl)-4-C-(2-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1.17 h / Cooling with ice

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

3.1: sodium periodate / 1,4-dioxane; water / 1.67 h

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

5.1: triethylamine / dichloromethane; methanol / 18 h / 0 - 20 °C

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

7.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C

7.2: 16.33 h / -78 - 20 °C

8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

8.2: 4 h / 50 °C

With sodium periodate; n-butyllithium; oxalyl dichloride; water; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;