O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 142657-31-6
• Molecular Formula: C₄₅H₅₂Cl₃NO₂₁
• Molecular Weight: 1049.26
• Mol file: 142657-31-6.mol

Synonyms:

Chemical Property of O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

There total 10 articles about O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 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: 82.0%

O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α/β-D-glucopyranoside (142657-40-7,142759-85-1) + trichloroacetonitrile (545-06-2) → O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (142657-31-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 5h; Ambient temperature;

Reference yield:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (128376-91-0,869848-87-3) → O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (142657-31-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 51 percent / molecular sieves 4 Angstroem, TMSOTF / CH₂Cl₂ / 1 h / Ambient temperature

2: 95 percent / trimethylsilyl trifluoromethanesulfonate, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 95 percent / Bu₄NF / CH₂Cl₂ / 1.5 h / 0 °C

4: 82 percent / DBU / CH₂Cl₂ / 5 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

Reference yield:

1,2,3,4-tetra-O-acetyl-D-fucopyranose (51921-33-6) → O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (142657-31-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / hydrazinium acetate / dimethylformamide / 0.42 h / 50 °C

2: 84 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

3: 95 percent / trimethylsilyl trifluoromethanesulfonate, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.67 h / Ambient temperature

4: 95 percent / Bu₄NF / CH₂Cl₂ / 1.5 h / 0 °C

5: 82 percent / DBU / CH₂Cl₂ / 5 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α/β-D-glucopyranoside

trichloroacetonitrile

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate

1,2,3,4-tetra-O-acetyl-D-fucopyranose

Downstream raw materials:

benzyl O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-(6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl)-(1->4)-(3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-6-deoxy-β-D-glucopyranoside

benzyl O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-(6-O-benzoyl-3-O-benzyl-β-D-glucopyranosyl)-(1->4)-(3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-6-deoxy-β-D-glucopyranoside