Sulfuric Acid → HCID 54149222, compound

HRID 1706576Notes

Reaction equation

HRID 1706576 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:14]([CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:13][CH:10]1[O:11]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(O)(=O)C>[CH2:1]([O:8][C@H:9]1[C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:15]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:14]([CH2:33][O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[O:13][CH:10]1[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 53940080HCID 53940080, compound

Product 1

HCID 54149222HCID 54149222, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The hydrolysis of methyl 2,3,4,6-tetra-O-benzyl-L-glucopyranoside may be carried out in glacial acetic acid and dilute sulphuric acid as formulated by Tate and Bishop (supra) to produce 2,3,4,6-tetra-O-benzyl-L-glucopyranose which can be reacted with thionyl chloride to form 2,3,4,6-tetra-O-benzyl-L-glucopyranosyl chloride. Halogenation of 2,3,4,6-tetra-O-benzyl-L-glucopyranose with zinc chloride-thionyl chloride results in a homogeneous 2,3,4,6-tetra-O-benzyl α-L-glucopyranosyl chloride product. In an alternative procedure, methyl 2,3,4,6-tetra-O-benzyl-α-L-glucopyranoside may be refluxed with thionyl chloride (48 hours at 5° C.) to produce 2,3,4,6-tetra-O-benzyl-L-glucopyranosyl chloride.

Sources & evidence

ORD record
ord-2de5c3a2d9d34a06823df5d2c337ee23
Source dataset
uspto-grants-1980_06
Patent number
US04207413

Reaction notes

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