51549-66-7

Upstream product

• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 262601-76-3 2,2,2-Trifluoro-N-[(R)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl]-acetamide 
• 262601-74-1 2,2,2-Trifluoro-acetimidic acid (E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester 
• 262601-86-5 2,2,2-Trifluoro-acetimidic acid (Z)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester 
• 663932-33-0 Methanesulfonic acid (Z)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester 
• 262601-80-9 (3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-((E)-3-thiocyanato-propenyl)-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 262601-79-6 (3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-((Z)-3-thiocyanato-propenyl)-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 262601-83-2 (3aR,5R,5aS,8aS,8bR)-5-((R)-1-Isothiocyanato-allyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 262601-81-0 (R)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allylamine 
• 100-39-0 benzyl bromide 
• 71553-88-3 metrhyl (Z)-6,7-dideoxyl-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-5-enopyranuronate 
• 262601-77-4 N-benzyl-2,2,2-trifluoro-N-[1-(2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl]-acetamide 
• 96796-56-4 1,2:3,4-di-O-isopropylidene-6,7-didehydro-α-D-galacto-oct-6(Z)-eno-1,5-pyranose 
• 663932-32-9 Methanesulfonic acid (E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester 

Downstream Products

• 51549-67-8 N-benzyl-N-[1-(2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl]-acetamide 

Relevant academic research and scientific papers

Stereocontrolled introduction of an amino group at C-6 of D-galactose via (3,3)-sigmatropic rearrangements - Novel synthesis of lincosamine and 7- epi-lincosamine precursors

A new and stereoselective route to the aminoglycoside components of the antibiotics lincomycin and clindamycin is presented. The key step involves diastereoselective introduction of the amino group at C-6 of D-galactose by (3,3)-sigmatropic rearrangements of the corresponding allylic (Z)- trifluoroacetimidate and (Z)- and (E)-allylic thiocyanates. Epoxidation of the resulting trifluoroacetamide with m-CPBA led to the epoxide with high threo-selectivity.