1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:709620-21-3
Molecular Formula:C₄₂H₄₁NO₉
Molecular Weight:703.789
Hs Code.:

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

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Chemical Property of 1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 4 articles about 1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 70.0%

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 168644-99-3
ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 709620-21-3
1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 0.333333h;
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

: 709620-21-3
1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

With N-iodo-succinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; 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

: 709620-21-3
1-O-[(1'R,4'S)-4'-acetoxycyclopent-2'-enyl]-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 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

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