methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

Base Information

Chemical Name:methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside
CAS No.:1332641-38-9
Molecular Formula:C₄₉H₅₃NO₉
Molecular Weight:799.961
Hs Code.:

Synonyms:methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

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Chemical Property of methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

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Technology Process of methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

There total 3 articles about methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside 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: 43.0%

: 136377-76-9
methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

: 1332641-35-6
2,3,4,6-tetra-O-benzyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosyl bromide

: methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

: 1332641-38-9
methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 75 ℃; for 14h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.bmcl.2011.07.046

Reference yield:

: 99695-34-8
(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

: methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

: 1332641-38-9
methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: carbon tetrabromide / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: tetrabutylammomium bromide / dichloromethane / 10 h / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 14 h / 75 °C / Inert atmosphere

With carbon tetrabromide; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; 1.1: Appel reaction;
DOI:10.1016/j.bmcl.2011.07.046

Reference yield:

: 1332641-33-4
2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

: methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

: 1332641-38-9
methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutylammomium bromide / dichloromethane / 10 h / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 14 h / 75 °C / Inert atmosphere

With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;
DOI:10.1016/j.bmcl.2011.07.046