D-(+)-Cellobiose (CNP0226604.15) → Sorbitol

HRID 1500132Notes

Reaction equation

HRID 1500132 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH2:13]([OH:35])[C@H:14]1[O:19][C@@H:18]([O:20][C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H:17]([OH:32])[C@@H:16]([OH:33])[C@@H:15]1[OH:34]>>[OH:12][CH2:11][C@@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10].[CH2:18]([OH:20])[C@H:17]([C@H:16]([C@@H:15]([C@@H:14]([CH2:13][OH:35])[OH:19])[OH:34])[OH:33])[OH:32]

Participants

4

Reactant 2

HCID 10712D-(+)-Cellobiose (CNP0226604.15)HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 2

HCID 5780SorbitolHCID 6251Mannitol

Procedure

The yield for the C6 compounds (sorbitol, mannitol and glucose) was calculated relative to the concentration of glucose and cellobiose in the reaction solution prior to the reaction. The C6 sugar alcohol yield (sorbitol, mannitol) was 84.0%, the glucose yield was 13.4%. The yield for xylitol (84.2%) and xylose (11.7%) were calculated relative to the concentration of xylose in the reaction solution prior to the reaction. Furthermore, glycerol, 1,3-propanediol, methanol, levulinic acid, hydroxymethylfurfural and furfural and furan acid were identified as by-products.

Workup

  1. customto the reaction

Sources & evidence

ORD record
ord-bfca1440d9544009bfe703a4fb5ec4ef
Source dataset
uspto-grants-2015_12
Patent number
US09206098B2

Reaction notes

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