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

Base Information

Chemical Name:ethyl 4,5,7-tri-O-benzyl-1,2,3-trideoxy-1-ethoxysulfonyl-2-thio-α-D-arabino-hept-2-ulopyranoside
CAS No.:946847-71-8
Molecular Formula:C₃₂H₄₀O₇S₂
Molecular Weight:600.797
Hs Code.:

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

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Chemical Property of ethyl 4,5,7-tri-O-benzyl-1,2,3-trideoxy-1-ethoxysulfonyl-2-thio-α-D-arabino-hept-2-ulopyranoside

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Technology Process of ethyl 4,5,7-tri-O-benzyl-1,2,3-trideoxy-1-ethoxysulfonyl-2-thio-α-D-arabino-hept-2-ulopyranoside

There total 2 articles about ethyl 4,5,7-tri-O-benzyl-1,2,3-trideoxy-1-ethoxysulfonyl-2-thio-α-D-arabino-hept-2-ulopyranoside 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: 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:

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

: 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:: Multi-step reaction with 2 steps

1.1: (i-Pr)2NH; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -60 °C

1.2: 88 percent / hexane; tetrahydrofuran / 3 h / -60 - 20 °C

2.1: 74 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -20 °C

With n-butyllithium; boron trifluoride diethyl etherate; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.carres.2007.05.006

Reference yield: 57.0%

: 67-56-1
methanol

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

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

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

Guidance literature:: methanol; ethyl 4,5,7-tri-O-benzyl-1,2,3-trideoxy-1-ethoxysulfonyl-2-thio-α-D-arabino-hept-2-ulopyranoside; With 3 A molecular sieve; In dichloromethane; at 20 ℃; for 3h;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane; at -50 ℃; for 0.333333h; Further stages.;
DOI:10.1016/j.carres.2007.05.006