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

Base Information

Chemical Name:5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(3-propynyl)-α-D-ribofuranose
CAS No.:1092803-02-5
Molecular Formula:C₃₈H₄₂O₅Si
Molecular Weight:606.834
Hs Code.:

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

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

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

There total 10 articles about 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(3-propynyl)-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: 81.0%

: 1092803-40-1
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(3-propynyl)-α-D-ribofuranose

: 939-26-4
2-bromomethylnaphthyl bromide

: 1092803-02-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(3-propynyl)-α-D-ribofuranose

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 4h;
DOI:10.1021/ja105875e

Reference yield:

: 956485-06-6
3-O-(2-naphthylmethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 1092803-02-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(3-propynyl)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 12 steps

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

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

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

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

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

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

6.2: 16.33 h / -78 - 20 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

7.2: 4 h / 50 °C

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

8.2: 0.5 h

9.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

9.2: 2 h / -78 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C

11.1: tetrahydrofuran; hexanes / 0.5 h / -78 °C

12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C

With sodium periodate; n-butyllithium; oxalyl dichloride; water; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; 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

: 1092803-02-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(3-propynyl)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 10 steps

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

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

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

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

4.2: 16.33 h / -78 - 20 °C

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

5.2: 4 h / 50 °C

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

6.2: 0.5 h

7.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

7.2: 2 h / -78 °C

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C

9.1: tetrahydrofuran; hexanes / 0.5 h / -78 °C

10.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C

With n-butyllithium; oxalyl dichloride; water; sodium hydride; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; methanol; hexanes; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;