2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide

Base Information

• Chemical Name: 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide
• CAS No.: 478687-10-4
• Molecular Formula: C₅₁H₆₁N₃O₂₀
• Molecular Weight: 1036.05
• Mol file: 478687-10-4.mol

Synonyms:2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide

Chemical Property of 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide

There total 5 articles about 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide 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: 60.0%

O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide (226707-92-2) + phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside (478687-09-1) → 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (478687-10-4)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -30 ℃; for 2h;

DOI:10.1016/S0008-6215(02)00159-3

Reference yield:

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (97974-20-4) → 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (478687-10-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-(dimethylamino)-pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 400 mg / Bu₃SnH; AIBN / benzene / 1 h / 80 °C

3: 60 percent / N-iodosuccinimide; triflic acid; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -30 °C

With dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; 4 A molecular sieve; tri-n-butyl-tin hydride; In dichloromethane; benzene; 2: Barton-McCombie deoxygenation;

DOI:10.1016/S0008-6215(02)00159-3

Reference yield:

phenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside → 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (478687-10-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaH / dimethylformamide / 0 - 20 °C

2: 53 percent / HCl; NaCNBH₃; 4 Angstroem molecular sieves / tetrahydrofuran; diethyl ether / 0.33 h

3: 4-(dimethylamino)-pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

4: 400 mg / Bu₃SnH; AIBN / benzene / 1 h / 80 °C

5: 60 percent / N-iodosuccinimide; triflic acid; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -30 °C

With hydrogenchloride; dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; 4 A molecular sieve; tri-n-butyl-tin hydride; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 4: Barton-McCombie deoxygenation;

DOI:10.1016/S0008-6215(02)00159-3

upstream raw materials:

O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide

phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Downstream raw materials:

2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-N-acetyl-2,3,6-tri-O-acetyl-β-D-glucopyranosylamine