(1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol

Base Information

• Chemical Name: (1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol
• CAS No.: 132335-80-9
• Molecular Formula: C₄₅H₄₆O₁₇
• Molecular Weight: 858.85
• Mol file: 132335-80-9.mol

Synonyms:

Chemical Property of (1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol

There total 5 articles about (1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol 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:

5-hydroxy-2,2-diphenylnaphtho<1,2-d>-1,3-dioxole-6,9-dione (97467-30-6) → (1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol (132335-80-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / benzene / Heating

3: toluene-p-sulfonic acid

With toluene-4-sulfonic acid; In benzene;

DOI:10.1039/c39890000017

Reference yield:

(E)-4-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)but-3-en-2-one (88204-85-7) → (1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol (132335-80-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / Zn, TiCl₄ / tetrahydrofuran

2: 54 percent / benzene / Heating

4: toluene-p-sulfonic acid

With titanium tetrachloride; toluene-4-sulfonic acid; zinc; In tetrahydrofuran; benzene;

DOI:10.1039/c39890000017

Reference yield:

oxobis<(1R,2S,3R,4aR,9aR)-1,2,3,4,4a,9a-hexahydro-5,6,8-trihydroxy-3-methyl-9,10-dioxo-5,6-O-diphenylmethylidene-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3-diolato>osmium(VI) (132335-79-6) + 2,2-dimethoxy-propane (77-76-9) → (1R,2S,3R,4aR,9aR)-5,6-O-diphenylmethylidene-1,2,3,4,4a,9a-hexahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol (132335-80-9)

Guidance literature:

With hydrogen sulfide; toluene-4-sulfonic acid; Yield given. Multistep reaction; 1) CH₂Cl₂, 2) 1 h;

DOI:10.1016/S0040-4020(01)85591-5

upstream raw materials:

oxobis<(1R,2S,3R,4aR,9aR)-1,2,3,4,4a,9a-hexahydro-5,6,8-trihydroxy-3-methyl-9,10-dioxo-5,6-O-diphenylmethylidene-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3-diolato>osmium(VI)

2,2-dimethoxy-propane

5-hydroxy-2,2-diphenylnaphtho<1,2-d>-1,3-dioxole-6,9-dione

(1S,4aR,9aR)-5,6-O-diphenylmethylidene-1,4,4a,9a-tetrahydro-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-5,6,8-triol

Downstream raw materials:

(+)-bostrycin

(1R,2S,3R)-5,6-O-diphenylmethylidene-1,2,3,4-tetrahydro-2,3-O-isopropylidene-3-methyl-9,10-dioxo-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)anthracene-2,3,5,6,8-pentaol