5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

Chemical Name:5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose
CAS No.:851981-55-0
Molecular Formula:C₃₀H₅₀O₄
Molecular Weight:474.725
Hs Code.:

Synonyms:5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

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Chemical Property of 5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

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Technology Process of 5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

There total 8 articles about 5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-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%

: 100-44-7
benzyl chloride

: 851982-08-6
(R)-2-((3aR,5R,6R,6aR)-2,2-Dimethyl-5-tridecyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-propan-1-ol

: 851981-55-0
5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: (R)-2-((3aR,5R,6R,6aR)-2,2-Dimethyl-5-tridecyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-propan-1-ol; With sodium hydride; In N,N-dimethyl-formamide; at 80 - 100 ℃; for 1h;

benzyl chloride; In N,N-dimethyl-formamide; at 22 ℃; for 12h;
DOI:10.1002/ejoc.200400653

Reference yield:

: 19029-63-1
3-C-(carbomethoxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

: 851981-55-0
5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: Pb(OAc)4 / CH₂Cl₂ / 22 °C

2.1: 6.60 g / tetrahydrofuran / 14 h / 22 °C

3.1: 98 percent / H₂ / Pd/C / methanol; ethyl acetate / 22 °C / 1500.12 Torr

4.1: lithium diisopropylamide / tetrahydrofuran / 3 h / -50 °C

4.2: 96 percent / tetrahydrofuran / -78 - 20 °C

5.1: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 22 °C

6.1: sodium hydride / dimethylformamide / 1 h / 80 - 100 °C

6.2: 81 percent / dimethylformamide / 12 h / 22 °C

With lead(IV) acetate; lithium aluminium tetrahydride; hydrogen; sodium hydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200400653

Reference yield:

: 54208-04-7
dodecylidenetriphenylphosphorane

: 851981-55-0
5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: 6.60 g / tetrahydrofuran / 14 h / 22 °C

2.1: 98 percent / H₂ / Pd/C / methanol; ethyl acetate / 22 °C / 1500.12 Torr

3.1: lithium diisopropylamide / tetrahydrofuran / 3 h / -50 °C

3.2: 96 percent / tetrahydrofuran / -78 - 20 °C

4.1: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 22 °C

5.1: sodium hydride / dimethylformamide / 1 h / 80 - 100 °C

5.2: 81 percent / dimethylformamide / 12 h / 22 °C

With lithium aluminium tetrahydride; hydrogen; sodium hydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200400653