alpha-Acetobromogalactose → (2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 1486461Notes

Reaction equation

HRID 1486461 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@@H:6]1Br)(=O)C.[Br-].C(O[C@@H]1[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1SC(N)=[NH2+])(=[O:28])C.C(O[C@@H]1[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1SCC#N)(=O)C>>[O:20]=[CH:19][C@@H:8]([C@H:9]([C@H:10]([C@@H:5]([CH2:6][OH:28])[OH:4])[OH:11])[OH:15])[OH:7]

Participants

4

Reactant 3

HCID 2734143alpha-AcetobromogalactoseHCID 18634526HCID 18634526, compoundHCID 8669893751224-13-6

Product 1

HCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Procedure

The galactose coupling agent 2-imino-2-methoxyethyl-1-thio-β-D-galactopyranoside (9) was prepared starting from 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (6) in 3 steps via the intermediates 2-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-thiouronium bromide (7) and cyanomethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (8) as shown in FIG. 5.

Sources & evidence

ORD record
ord-d0651a71b4ee49ab9375955a96e518e4
Source dataset
uspto-grants-2016_08
Patent number
US09427482B2

Reaction notes

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