(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7-(dimethylamino)-8-hydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

Base Information

• Chemical Name: (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7-(dimethylamino)-8-hydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• CAS No.: 105655-99-0
• Molecular Formula: C₃₁H₃₇NO₁₂
• Molecular Weight: 615.634
• UNII: VLN3VGF679
• Nikkaji Number: J524.973B
• Mol file: 105655-99-0.mol

Synonyms:NK 611;NK-611;NK611

Chemical Property of (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7-(dimethylamino)-8-hydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

Chemical Property:

• PSA: 143.84000
• Density: 1.46
• LogP: 1.90790
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 615.23157562
• Heavy Atom Count: 44
• Complexity: 1020

Purity/Quality:

99% ^*data from raw suppliers

NK-611 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)N(C)C)O
• Isomeric SMILES: C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)N(C)C)O

Technology Process of (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7-(dimethylamino)-8-hydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

There total 46 articles about (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7-(dimethylamino)-8-hydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-O-(2-amino-2-deoxy-4,6-O-ethylidene-β-D-glucopyranosyl)-4'-O-demethyl-4-epipodophyllotoxin (105656-01-7) → 4'-O-demethyl-4-O-(2-deoxy-2-dimethylamino-4,6-O-ethylidene-β-D-glucopyranosyl)-4-epipodophyllotoxin (105655-99-0,112246-52-3,112246-53-4,112246-54-5,131177-36-1)

Guidance literature:

With sodium cyanoborohydride; In methanol; water; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(90)80062-8

Reference yield: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-O-(2-amino-2-deoxy-4,6-O-ethylidene-α-D-glucopyranosyl)-4'-O-demethyl-4-epipodophyllotoxin (105656-01-7,111322-27-1,112146-42-6,112246-51-2,112317-52-9,112318-79-3,134623-83-9) → 4'-O-demethyl-4-O-(2-deoxy-2-dimethylamino-4,6-O-ethylidene-α-D-glucopyranosyl)-4-epipodophyllotoxin (105655-99-0,112246-52-3,112246-53-4,112246-54-5,131177-36-1)

Guidance literature:

With sodium cyanoborohydride; In methanol; water; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(90)80062-8

Reference yield: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4′-demethyl-(epi)-podophyllotoxin 4-O-2″-deoxy-2″-amino-4″,6″-di-O-ethylidene-β-D-glucopyranoside (112146-42-6) → 1-O-(2-deoxy-2-dimethylamino-β-D-glucopyranosyl)-<(-)-1-epipodophyllotoxin> (105655-99-0,112246-52-3,112246-53-4,112246-54-5,131177-36-1)

Guidance literature:

With sodium cyanoborohydride; In methanol; water; at 20 ℃; for 4h;

DOI:10.1021/acs.joc.7b00485

upstream raw materials:

formaldehyd

4-O-(2-amino-2-deoxy-4,6-O-ethylidene-β-D-glucopyranosyl)-4'-O-demethyl-4-epipodophyllotoxin

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin

4'-O-benzyloxycarbonyl-4-O-(2-benzyloxycarbonylamino-2-deoxy-4,6-O-ethylidene-β-D-glucopyranosyl)-4'-O-demethyl-4-epipodophyllotoxin