N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside

Base Information

• Chemical Name: N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside
• CAS No.: 1160510-81-5
• Molecular Formula: C₃₉H₄₈N₂O₁₁
• Molecular Weight: 720.817
• Mol file: 1160510-81-5.mol

Synonyms:N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside

Chemical Property of N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside

There total 1 articles about N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside 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: 96.0%

3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) + allyl (2S,3R)-2-(tert-butoxycarbonylamino)-3-hydroxybutanoate (545432-97-1) → N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside (1160510-81-5)

Guidance literature:

3,4,6-tri-O-benzyl-2-nitro-D-galactal; With 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride; caesium carbonate; In tetrachloromethane; hexane; at 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

allyl (2S,3R)-2-(tert-butoxycarbonylamino)-3-hydroxybutanoate; In tetrachloromethane; hexane; at 20 ℃; for 10h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.7b02543

Reference yield: 87.0%

N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside (1160510-81-5) + acetic anhydride (108-24-7) → N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-acetamido-8-α-D-galactopyranoside

Guidance literature:

N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside; With hydrogenchloride; acetic acid; zinc; In tetrahydrofuran; water; at 0 ℃; for 3h; Inert atmosphere;

acetic anhydride; With pyridine; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02543

Reference yield: 87.0%

N-Boc-L-threonine allyl ester 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside (1160510-81-5) → C36H44N2O11 (1160510-84-8)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 3h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/chem.200801777

upstream raw materials:

3,4,6-tri-O-benzyl-2-nitro-D-galactal

allyl (2S,3R)-2-(tert-butoxycarbonylamino)-3-hydroxybutanoate

Downstream raw materials:

C₃₆H₄₄N₂O₁₁

C₂HF₃O₂*C₃₄H₄₀N₂O₉