Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

Base Information

Chemical Name:Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester
CAS No.:851981-56-1
Molecular Formula:C₃₄H₅₆O₇
Molecular Weight:576.814
Hs Code.:

Synonyms:Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

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Chemical Property of Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

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Technology Process of Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

There total 7 articles about Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester 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: 83.0%

: 108-24-7
acetic anhydride

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

: 851981-56-1
Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 22 ℃; for 5h;
DOI:10.1002/ejoc.200400653

Reference yield:

: 54208-04-7
dodecylidenetriphenylphosphorane

: 851981-56-1
Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

Guidance literature:: Multi-step reaction with 6 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

6.1: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / 22 °C

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; 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:

: 15510-55-1
dodecyltriphenylphosphonium bromide

: 851981-56-1
Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran

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

7.1: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / 22 °C

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