4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

Base Information

Chemical Name:4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose
CAS No.:946847-69-4
Molecular Formula:C₃₀H₃₆O₈S
Molecular Weight:556.677
Hs Code.:

Synonyms:4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

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Chemical Property of 4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

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Technology Process of 4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

There total 1 articles about 4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose 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: 88.0%

: 79999-46-5,72605-77-7
(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one

: 62-50-0
Ethyl methanesulfonate

: 946847-69-4
4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

Guidance literature:: Ethyl methanesulfonate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -60 ℃; for 0.25h;

(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 3h; Further stages.;
DOI:10.1016/j.carres.2007.05.006

Reference yield: 74.0%

: 946847-69-4
4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

: 75-08-1
ethanethiol

: 946847-71-8
ethyl 4,5,7-tri-O-benzyl-1,2,3-trideoxy-1-ethoxysulfonyl-2-thio-α-D-arabino-hept-2-ulopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 1.5h;
DOI:10.1016/j.carres.2007.05.006

Reference yield:

: 946847-69-4
4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

: methyl 4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 74 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -20 °C

2.1: 3 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

2.2: 57 percent / NIS; TfOH / tetrahydrofuran; CH₂Cl₂ / 0.33 h / -50 °C

With 3 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1016/j.carres.2007.05.006