(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol

Base Information

Chemical Name:(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol
CAS No.:655237-59-5
Molecular Formula:C₄₁H₄₁FO₆
Molecular Weight:648.771
Hs Code.:

Synonyms:(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol

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Chemical Property of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol

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Technology Process of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol

There total 4 articles about (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol 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: 58.0%

: 2,3,4,6-tetra-O-benzyl-1-C-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-D-glucopyranose

: 655237-59-5
(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol

Guidance literature:: With chlorotriisopropylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -40 ℃; for 2h; stereoselective reaction;
DOI:10.1016/j.bmc.2013.03.067

Reference yield:

: 655237-57-3
((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane

: 655237-59-5
(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 1 h / -78 °C

2.1: boron trifluoride diethyl etherate; chlorotriisopropylsilane / acetonitrile / 2 h / -40 °C

With n-butyllithium; chlorotriisopropylsilane; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; acetonitrile;
DOI:10.1016/j.bmc.2013.03.067

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 655237-59-5
(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-fluoro-5-(hydroxymethyl)phenyl]-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 1 h / -78 °C

2.1: boron trifluoride diethyl etherate; chlorotriisopropylsilane / acetonitrile / 2 h / -40 °C

With n-butyllithium; chlorotriisopropylsilane; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; acetonitrile;
DOI:10.1016/j.bmc.2013.03.067