8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide

Base Information

• Chemical Name: 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide
• CAS No.: 106444-77-3
• Molecular Formula: C₃₅H₄₈O₉
• Molecular Weight: 612.761
• Mol file: 106444-77-3.mol

Synonyms:

Chemical Property of 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide

There total 7 articles about 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide 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:

benzyl bromide (100-39-0) → 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide (106444-77-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / NaH (80percent in oil) / benzene / 16 h / Heating

2: LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 1.17 h / Heating

3: 98 percent / pyridine / Ambient temperature

4: 77 percent / conc. H₂SO₄ / 1) 0 deg C, 10 min, 2) RT, 25 min.

5: HBr (gas; through a tube of CaSO₄) / CH₂Cl₂ / 0 °C

6: 1) silver silicate/alumina / 1) CH₂Cl₂, RT, 1 h, 2) CH₂Cl₂, -78 deg C, 2.5 h then 10 h, RT

With pyridine; aluminum oxide; lithium aluminium tetrahydride; aluminium trichloride; silver silicate; sulfuric acid; hydrogen bromide; sodium hydride; In diethyl ether; dichloromethane; benzene;

Reference yield:

methyl 3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside (82228-10-2) → 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide (106444-77-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / NaH (80percent in oil) / benzene / 16 h / Heating

2: LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 1.17 h / Heating

3: 98 percent / pyridine / Ambient temperature

4: 77 percent / conc. H₂SO₄ / 1) 0 deg C, 10 min, 2) RT, 25 min.

5: HBr (gas; through a tube of CaSO₄) / CH₂Cl₂ / 0 °C

6: 1) silver silicate/alumina / 1) CH₂Cl₂, RT, 1 h, 2) CH₂Cl₂, -78 deg C, 2.5 h then 10 h, RT

With pyridine; aluminum oxide; lithium aluminium tetrahydride; aluminium trichloride; silver silicate; sulfuric acid; hydrogen bromide; sodium hydride; In diethyl ether; dichloromethane; benzene;

Reference yield:

1,6-Di-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranose (86861-45-2) → 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide (106444-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr (gas; through a tube of CaSO₄) / CH₂Cl₂ / 0 °C

2: 1) silver silicate/alumina / 1) CH₂Cl₂, RT, 1 h, 2) CH₂Cl₂, -78 deg C, 2.5 h then 10 h, RT

With aluminum oxide; silver silicate; hydrogen bromide; In dichloromethane;

upstream raw materials:

methyl 9-hydroxynonanoate

6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide

benzyl bromide

methyl 3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside

Downstream raw materials:

8-methoxycarbonyloctyl 6-o-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3-O-allyl-2,4-di-O-benzyl-β-D-mannopyranoside

8-methoxycarbonyloctyl 3-O-allyl-2,4-di-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-β-D-mannopyranoside

8-methoxycarbonyloctyl 3-O-allyl-2,4-di-O-benzyl-β-D-mannopyranoside

8-methoxycarbonyloctyl 3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranoside