68354-92-7

Usage

InChI:InChI=1/C39H68O6S/c1-25(2)11-10-12-26(3)30-15-16-31-29-14-13-27-23-28(17-19-38(27,4)32(29)18-20-39(30,31)5)44-21-8-6-7-9-22-46-37-36(43)35(42)34(41)33(24-40)45-37/h13,25-26,28-37,40-43H,6-12,14-24H2,1-5H3/t26-,28+,29?,30-,31?,32?,33-,34+,35+,36-,37+,38+,39-/m1/s1

Upstream product

• 68354-86-9 6-(5-cholesten-3β-yloxy)-1-iodohexane 
• 19879-84-6 tetraacetyl thioglucose 
• 68354-89-2 6-(5-cholesten-3β-yloxy)hexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 66965-73-9 sodium salt of 1-thio-α-D-mannose 

Relevant academic research and scientific papers

Glycolipids as host resistance stimulators

6-(5-Cholesten-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside (L-644,257) enhances natural host resistance in cyclophosphamide-treated mice against Pseudomonas aeruginosa in a dose-dependent manner. It is active sc, im, and ip but not orally. L-644,257 is substantially more protective against P. aeruginosa than its α anomer. The β-L-fucose glycolipid is more effective when given im and ip than sc. The lactose and β-D-glucose glycolipids were only marginally effective to nonprotective. The 17β-steroidal side chain of L-644,257 can be modified without substantial loss of protective activity.

Cell surface carbohydrates for targeting studies

Syntheses of a series of glycolipids with 6-(5-cholesten-3β-yloxy)-1-thiohexane as the aglycon and the following carbohydrates as surface determinants are described: D-glucose, D-mannose, D-galactose, 2-acetamido-2deoxy-D-glucose, 2-acetamido-2-deoxy-D-galactose, L-fucose, L-arabinose, D-xylose, N-acetyl-D-neuraminic acid, lactose, and cellobiose.These 6-(5-cholesten-3β-yloxy)hexyl 1-thioglycopyranosides have been incorporated into phospholipid vesicles for in vivo tissue distribution studies.