Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside

Base Information

• Chemical Name: Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside
• CAS No.: 182167-87-9
• Molecular Formula: C₃₆H₃₈O₁₂
• Molecular Weight: 662.691
• Mol file: 182167-87-9.mol

Synonyms:Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside

Chemical Property of Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside

There total 19 articles about Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside 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: 88.0%

Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside (182167-86-8) → Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside (182167-87-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; at 60 ℃; for 3h;

DOI:10.1080/07328309608005684

Reference yield:

benzoyl chloride (98-88-4) → Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside (182167-87-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / pyridine / 1 h / Ambient temperature

2: 84 percent / H₂SO₄ / 0.75 h / 0 °C

3: SnCl₄ / CH₂Cl₂ / 2 h / Ambient temperature

4: 93 percent / NIS, TfOH / 1,2-dichloro-ethane; diethyl ether / 0.25 h / -30 °C

5: 88 percent / HCl / dioxane; methanol / 3 h / 60 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; sulfuric acid; tin(IV) chloride; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1080/07328309608005684

Reference yield:

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (112612-45-0) → Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside (182167-87-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / NaH / dimethylformamide / 2 h / Ambient temperature

2: 75 percent / LiAlH₄ / diethyl ether / 2 h / Heating

3: 80 percent / 50percent aq. AcOH / 1 h / 60 °C

4: pyridine, SOCl₂ / ethyl acetate / 0.5 h / 0 °C

5: aq. NaIO₄, RuCl₃ / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

7: 93 percent / DDQ, H₂O / CH₂Cl₂ / 2 h / Ambient temperature

8: 95 percent / pyridine / 1 h / Ambient temperature

9: 84 percent / H₂SO₄ / 0.75 h / 0 °C

10: SnCl₄ / CH₂Cl₂ / 2 h / Ambient temperature

11: 93 percent / NIS, TfOH / 1,2-dichloro-ethane; diethyl ether / 0.25 h / -30 °C

12: 88 percent / HCl / dioxane; methanol / 3 h / 60 °C

With pyridine; hydrogenchloride; ruthenium trichloride; sodium periodate; N-iodo-succinimide; lithium aluminium tetrahydride; thionyl chloride; trifluorormethanesulfonic acid; sulfuric acid; water; tin(IV) chloride; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005684

upstream raw materials:

Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside

Methyl 2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranoside

benzoyl chloride

allyl 2,3-O-isopropylidene-α-D-mannopyranoside