(1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:1197032-95-3
Molecular Formula:C₂₈H₃₄N₂O₆Si
Molecular Weight:522.673
Hs Code.:

Synonyms:(1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

There total 12 articles about (1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 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: 77.0%

: 1197032-94-2
(1S,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-6-methyl-7-(2-naphthylmethyloxy)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

: 1197032-95-3
(1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/jo902560f

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

: 1197032-95-3
(1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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 / 16 h / 0 - 20 °C

2.2: 2 h / 20 °C

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

3.2: 1 h / -78 °C / Cooling with ice

4.1: cerium(III) chloride / tetrahydrofuran / 1.58 h / 0 - 20 °C / Cooling with ice

4.2: 3 h / -78 °C

4.3: -78 - 20 °C

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

5.2: 1 h / -78 °C / Cooling with ice

6.1: lithium borohydride; methanol / tetrahydrofuran / 2 h / -78 °C

7.1: dmap; triethylamine / dichloromethane / 2.5 h / 0 °C

8.1: sulfuric acid; acetic acid / 3 h / 20 °C

9.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.25 h / 40 °C

9.2: 2 h / Cooling with ice; Reflux

9.3: 16 h / 20 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 16 h / 20 °C

With methanol; dmap; lithium borohydride; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; oxalyl dichloride; sulfuric acid; water; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile; 3.1: Swern Oxidation / 5.1: Swern Oxidation;

Reference yield:

(3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde: (3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 1197032-95-3
(1R,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-7-hydroxy-6-methyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 7 steps

1.1: cerium(III) chloride / tetrahydrofuran / 1.58 h / 0 - 20 °C / Cooling with ice

1.2: 3 h / -78 °C

1.3: -78 - 20 °C

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

2.2: 1 h / -78 °C / Cooling with ice

3.1: lithium borohydride; methanol / tetrahydrofuran / 2 h / -78 °C

4.1: dmap; triethylamine / dichloromethane / 2.5 h / 0 °C

5.1: sulfuric acid; acetic acid / 3 h / 20 °C

6.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.25 h / 40 °C

6.2: 2 h / Cooling with ice; Reflux

6.3: 16 h / 20 °C

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 16 h / 20 °C

With methanol; dmap; lithium borohydride; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; oxalyl dichloride; sulfuric acid; water; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetonitrile; 2.1: Swern Oxidation;