allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside

Base Information

• Chemical Name: allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside
• CAS No.: 282089-17-2
• Molecular Formula: C₅₇H₆₂O₁₁
• Molecular Weight: 923.113
• Mol file: 282089-17-2.mol

Synonyms:allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside

Chemical Property of allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside

There total 7 articles about allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-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: 33.0%

2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (74808-09-6,83441-60-5,90357-89-4,90358-01-3,103368-01-0,103368-04-3,103368-06-5,104048-30-8,104048-33-1,132201-75-3,132748-02-8,114743-70-3) + allyl 2,6-di-O-benzyl-α-D-galactopyranoside (37111-91-4) → allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside (282089-17-2) + allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranoside

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 24h;

DOI:10.1016/S0008-6215(00)00010-0

Reference yield:

benzyl bromide (100-39-0) → allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside (282089-17-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / KOH; tetraoctylammonium bromide / CH₂Cl₂ / 72 h / 20 °C

2: 92 percent / 1M aq. HCl / methanol / 1 h / 60 °C

3: 33 percent / BF₃*OEt₂; molecular sieves (4 Angstroem) / CH₂Cl₂ / 24 h / -30 °C

With hydrogenchloride; potassium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; tetraoctyl ammonium bromide; In methanol; dichloromethane; 1: benzylation / 2: Hydrolysis / 3: glycosylation;

DOI:10.1016/S0008-6215(00)00010-0

Reference yield:

(2S,3R,4S,5R,6R)-2-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (48149-72-0,821794-45-0) → allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside (282089-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 53 percent / cc. H₂SO₄ / dimethylformamide / 17 h / 20 °C

2: 81 percent / KOH; tetraoctylammonium bromide / CH₂Cl₂ / 72 h / 20 °C

3: 92 percent / 1M aq. HCl / methanol / 1 h / 60 °C

4: 33 percent / BF₃*OEt₂; molecular sieves (4 Angstroem) / CH₂Cl₂ / 24 h / -30 °C

With hydrogenchloride; potassium hydroxide; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; tetraoctyl ammonium bromide; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: transetherification / 2: benzylation / 3: Hydrolysis / 4: glycosylation;

DOI:10.1016/S0008-6215(00)00010-0

upstream raw materials:

2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

allyl 2,6-di-O-benzyl-α-D-galactopyranoside

2-propenyl 2,3,4,6-tetra-O-benzyl-α-D-glactopyranoside

2,3,4,6-tetra-O-benzyl-D-galactopyranose

Downstream raw materials:

3-O-α-D-galactopyranosyl-α-D-galactopyranose