102716-65-4

Upstream product

• 1335028-91-5 (2R,5S)-2-(benzyloxy)-7-methyloct-7-ene-1,5-diol 
• 1335028-92-6 (3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-one 
• 1335028-93-7 (((2R,3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-yl)oxy)(tert-butyl)dimethylsilane 
• 1335028-94-8 (R)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 
• 115352-42-6 2-propyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside 
• 93662-86-3 isopropyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside 
• 102716-55-2 (2S,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-isopropoxy-tetrahydro-pyran-3-ol 
• 102716-53-0 2-Propyl 3,4-dideoxy-α-D-erythro-hexopyranoside 
• 100-39-0 benzyl bromide 
• 102716-64-3 (3R,6S)-3-Benzyloxy-2-(2-chloro-ethoxy)-6-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran 
• 102716-60-9 (E)-3-[(2S,5R)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol 
• 102716-62-1 (R)-3-[(2S,5R)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-propane-1,2-diol 
• 102716-57-4 (E)-3-((2S,5R,6S)-5-Benzyloxy-6-isopropoxy-tetrahydro-pyran-2-yl)-2-methyl-acrylic acid ethyl ester 

Downstream Products

• 102716-67-6 (3R,6S)-3-(benzyloxy)-6-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)tetrahydro-2H-pyran-2-one 
• 1335028-96-0 (2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one 
• 1335028-97-1 (2S,6R,8S,11R)-11-(benzyloxy)-2-((R)-1-((4-methoxybenzyl)oxy)propan-2-yl)-4-methyl-8-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-ene 
• 1335028-85-7 (S)-2-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)propanal 
• 1335028-84-6 (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one 
• 1335029-05-4 (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol 
• 1335029-06-5 (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid 
• 102716-73-4 Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl)-pentyl ester 
• 102795-11-9 (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one 
• 102795-14-2 (2S,6R,8S,11R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-11-benzyloxy-4-methyl-8-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl)-1,7-dioxa-spiro[5.5]undec-4-ene 
• 102795-10-8 (2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-11-methyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-yn-6-one 

Relevant academic research and scientific papers

Total synthesis of dinophysistoxin-2 and 2-epi-dinophysistoxin-2 and their PPase inhibition

The first total syntheses of the title compounds highlight novel assemblies of the C1-C14 and C28-C38 domains, including an unexpected diastereoselectivity in the Sharpless asymmetric dihydroxylation of an alkene at C1iC2. PPase inhibition assays revealed that 2-epi-DTX-2 is at least 1 to 2 orders of magnitude less potent than DTX-2, thus indicating that the configuration at C2 in DTX-2 is crucial for potent inhibition (see picture). Copyright

Synthesis of a marine polyether toxin, okadaic acid [1]1 1 Full Paper corresponding to the communications, M. Isobe, Y. Ichikawa and T. Goto, Tetrahedron Lett., 26, 5199 (1985); M. Isobe, Y. Ichikawa, D-L. Bai and T. Goto, Tetrahedron Lett., 26, 5203 (1985). - strategy and synthesis of segment a

The title compound was divided into three retrosynthetic segments A, B and C, by disconnecting two C-C bonds at C- 14 15 and C- 27 28. Segment A for okadaic acid synthesis comprises the carbon skeleton from C-1 through C-14, which was further disconnected at the bonds between C-8 and C-9 into two fragments A1 and A2. Each fragment was synthesized in the optically active form from D-glucose derivatives. Key steps are the oxymercuration and anti-selective heteroconjugate addition to elaborate the asymmetric carbons on acyclic parts of these fragments. The coupling was facilitated between the acetylenic carbanion and the lactone carbonyl of the respective fragments. The segment A was synthesized in 36 steps.

Synthetic studies toward marine toxic polyethers. 3. Stereocontrol for segment-A1 of okadaic acid by means of oxymercuration and epoxydation

Segment-A1 of okadaic acid was synthesized from glucose via an acyclic stereocontrol for C-2 by means of oxymercuration. The stereochemistry was proven by comparison with S and R epoxides which were synthesized selectively by chelational and st