O³-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N²-(benzyloxycarbonyl)-L-serine allyl ester

Base Information

• Chemical Name: O³-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N²-(benzyloxycarbonyl)-L-serine allyl ester
• CAS No.: 88287-93-8
• Molecular Formula: C₄₀H₄₃NO₉
• Molecular Weight: 681.783

Synonyms:O³-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N²-(benzyloxycarbonyl)-L-serine allyl ester

Chemical Property of O³-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N²-(benzyloxycarbonyl)-L-serine allyl ester

Chemical Property:

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Technology Process of O³-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N²-(benzyloxycarbonyl)-L-serine allyl ester

There total 5 articles about O³-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N²-(benzyloxycarbonyl)-L-serine allyl ester 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: 9.0%

N-(benzyloxycarbonyl)serine allyl ester (88295-41-4) + 1-O-(trichloroacetimidoyl)-2,3,4-tri-O-benzyl-α-D-xylopyranose (83441-63-8) → O3-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N2-(benzyloxycarbonyl)-L-serine allyl ester (88287-93-8) + O3-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-N2-(benzyloxycarbonyl)-L-serine allyl ester (88287-92-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 1h;

DOI:10.1021/jo00265a007

Reference yield:

2,3,4-tri-O-benzyl-D-xylopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1) → O3-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N2-(benzyloxycarbonyl)-L-serine allyl ester (88287-93-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine / 24 h

2: 100 percent / liq. HF / CH₂Cl₂ / 0.5 h / -70 °C

3: 67 percent Chromat_. / BF₃*Et₂O, Et₃N / CH₂Cl₂ / 0.5 h

With boron trifluoride diethyl etherate; hydrogen fluoride; triethylamine; In pyridine; dichloromethane;

DOI:10.1002/hlca.19850680134

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → O3-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-N2-(benzyloxycarbonyl)-L-serine allyl ester (88287-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 6percent NaHCO₃, methyltrioctylammoniumchloride / CH₂Cl₂

2: 56 percent / BF₃ / -30 °C

With boron trifluoride; Aliquat 336; sodium hydrogencarbonate; In dichloromethane;

upstream raw materials:

N-(benzyloxycarbonyl)serine allyl ester

1-O-(trichloroacetimidoyl)-2,3,4-tri-O-benzyl-α-D-xylopyranose

2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride

2,3,4-tri-O-benzyl-D-xylopyranose

Downstream raw materials:

N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serylalanylalanylglycylalanine allyl ester

N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serylalanylalanine allyl ester

N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serylalanylalanine

N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serine

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