3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate

Base Information

Chemical Name:3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate
CAS No.:302800-99-3
Molecular Formula:C₃₈H₄₆O₉
Molecular Weight:646.778
Hs Code.:

Synonyms:3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate

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Chemical Property of 3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate

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Technology Process of 3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate

There total 6 articles about 3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate 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%

: 102208-53-7
(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

: 302801-28-1
5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylofuranosiduronic acid

: 302800-99-3
3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;
DOI:10.1021/jo0005159

Reference yield:

: 70005-82-2,69984-00-5
ethyl (E)-[3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

: 302800-99-3
3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 1810.07 Torr

2: 97 percent / LiOH / tetrahydrofuran; H₂O / 20 °C / Saponification

3: 83 percent / 4-DMAP; DCC / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 1: Catalytic hydrogenation / 2: Hydrolysis / 3: Esterification;
DOI:10.1021/jo0005159

Reference yield:

: 18968-51-9,43138-66-5,63522-21-4,816444-37-8
1,2-O-isopropylidene-3-O-methyl-α-D-xylo-pentodialdo-1,4-furanose

: 302800-99-3
3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / benzene / 20 °C

2: 84 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 1810.07 Torr

3: 97 percent / LiOH / tetrahydrofuran; H₂O / 20 °C / Saponification

4: 83 percent / 4-DMAP; DCC / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; benzene; 1: Wittig reaction / 2: Catalytic hydrogenation / 3: Hydrolysis / 4: Esterification;
DOI:10.1021/jo0005159