allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS No.: 131267-32-8
• Molecular Formula: C₇₃H₈₆O₂₆
• Molecular Weight: 1379.47
• Mol file: 131267-32-8.mol

Synonyms:

Chemical Property of allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

There total 14 articles about allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 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: 50.0%

allyl O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (93752-84-2) + 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-α-D-xylopyranosyl bromide (131267-25-9) → C73H86O26 (131267-34-0) + allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (131267-32-8)

Guidance literature:

With 4 A molecular sieve; mercury dibromide; In 1,2-dichloro-ethane; 1.) 2 h, 0 deg C, 2.) room temperature, overnight;

DOI:10.1016/0008-6215(90)80143-Q

Reference yield: 50.0%

allyl O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (93752-84-2) + 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-α-D-xylopyranosyl chloride (131267-24-8) → C73H86O26 (131267-34-0) + allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (131267-32-8)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; 1.) 3 h, -15 deg C, 2.) room temperature, overnight;

DOI:10.1016/0008-6215(90)80143-Q

Reference yield:

(2S,3R,4R,5S,6R)-2-((2R,3R,4S,5R)-2-Allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (130136-33-3) → allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-xylopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (131267-32-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / potassium tert-butoxide / dimethylsulfoxide / 2 h / 60 °C

2: 86 percent / pyridine / 10 h / Ambient temperature

3: 88 percent / mercuric chloride, yellow mercuric oxide / acetone; H₂O / 0.25 h / Ambient temperature

4: 92 percent / oxalyl chloride, N,N-dimethylformamide / 1,2-dichloro-ethane / 2 h / Ambient temperature

5: 50 percent / silver triflate, 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 1.) 3 h, -15 deg C, 2.) room temperature, overnight

With pyridine; oxalyl dichloride; 4 A molecular sieve; potassium tert-butylate; silver trifluoromethanesulfonate; N,N-dimethyl-formamide; mercury dichloride; mercury(II) oxide; In water; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone;

DOI:10.1016/0008-6215(90)80143-Q

upstream raw materials:

allyl O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-α-D-xylopyranosyl chloride

2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-α-D-xylopyranosyl bromide

(2S,3R,4R,5S,6R)-2-((2R,3R,4S,5R)-2-Allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Downstream raw materials:

propyl O-β-D-galactopyranosyl-(1->2)-O-α-D-xylopyranosyl-(1->6)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside

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