benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate

Base Information

Chemical Name:benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate
CAS No.:856668-37-6
Molecular Formula:C₃₀H₃₉NO₁₃
Molecular Weight:621.639
Hs Code.:

Synonyms:benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate

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Chemical Property of benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate

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Technology Process of benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate

There total 7 articles about benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate 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: 80.0%

: 142980-15-2
benzyl 2-(tert-butyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate

: 193156-88-6
2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetaldehyde

: 856668-37-6
benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate

Guidance literature:: With N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol050677x

Reference yield:

: 856668-36-5
2-(tert-butyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetic acid

: 856668-37-6
benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: 69 percent / 4-DMAP; DCC / CH₂Cl₂ / 0 - 20 °C

2: 80 percent / TMG / tetrahydrofuran / 1 h / 20 °C

With dmap; dicyclohexyl-carbodiimide; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; dichloromethane; 2: Horner-Emmons olefination;
DOI:10.1021/ol050677x

Reference yield:

: 53263-18-6,82659-53-8,98920-46-8,98920-48-0,98920-49-1,103773-87-1,98920-44-6
allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

: 856668-37-6
benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 83 percent / PPh₃ / CH₂Cl₂

2.1: 80 percent / TMG / tetrahydrofuran / 1 h / 20 °C

With ozone; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; dichloromethane; 2.1: Horner-Emmons olefination;
DOI:10.1021/ol050677x