(4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene

Base Information

Chemical Name:(4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene
CAS No.:709620-26-8
Molecular Formula:C₅₃H₄₉NO₁₁
Molecular Weight:875.972
Hs Code.:

Synonyms:(4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene

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Chemical Property of (4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene

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Technology Process of (4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene

There total 6 articles about (4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene 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: 60.0%

: 137434-21-0
2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylic acid

: 709620-23-5
1-O-[(1'R,4'S)-4'-hydroxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 709620-26-8
(4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tet.2004.03.021

Reference yield:

: 10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 709620-26-8
(4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / BF₃*Et₂O / CHCl₃ / 4 h / Heating

2: 90 percent / NaOMe / methanol / 4 h / 20 °C / pH 8

3: 60 percent / tetrabutylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

4: 70 percent / NIS; BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.33 h / -30 °C

5: 90 percent / K₂CO₃ / methanol / 3 h / pH 8

6: 60 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

With dmap; N-iodo-succinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.03.021

Reference yield:

: 130539-43-4
ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 709620-26-8
(4'R,1'S)-[4'-(2''-hydroxy-7''-methoxy-5''-methylnaphthoate)]-1'-O-[3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-1',4'-dihydroxycyclopentene

Guidance literature:: Multi-step reaction with 4 steps

1: 60 percent / tetrabutylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

2: 70 percent / NIS; BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.33 h / -30 °C

3: 90 percent / K₂CO₃ / methanol / 3 h / pH 8

4: 60 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

With dmap; N-iodo-succinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.03.021