ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate

Base Information

Chemical Name:ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate
CAS No.:474081-55-5
Molecular Formula:C₃₉H₄₂O₈
Molecular Weight:638.758
Hs Code.:

Synonyms:ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate

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Chemical Property of ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate

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Technology Process of ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate

There total 4 articles about ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate 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: 72.0%

: 623-73-4
diazoacetic acid ethyl ester

: 140397-47-3
2,6-anhydro-3,4,5,7-tetra-O-benzyl-aldehydo-D-glycero-D-galacto-heptopyranose

: 474081-55-5
ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo0202076

Reference yield: 10.0%

: 105-36-2
ethyl bromoacetate

: 188819-44-5
1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl cyanide

: 474081-55-5
ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate

Guidance literature:: ethyl bromoacetate; With zinc; In tetrahydrofuran; for 0.333333h; Inert atmosphere; Reflux;

1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl cyanide; In tetrahydrofuran; for 1h; Inert atmosphere; Reflux;

With hydrogenchloride; water; In tetrahydrofuran; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201800090

Reference yield:

: 3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9
1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose

: 474081-55-5
ethyl 3-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-3-oxopropanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: zinc trifluoromethanesulfonate / acetonitrile / 1 h / 20 °C / Inert atmosphere

2.1: zinc / tetrahydrofuran / 0.33 h / Inert atmosphere; Reflux

2.2: 1 h / Inert atmosphere; Reflux

2.3: 1 h / Inert atmosphere

With zinc trifluoromethanesulfonate; zinc; In tetrahydrofuran; acetonitrile;
DOI:10.1002/ejoc.201800090