4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose

Base Information

• Chemical Name: 4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose
• CAS No.: 109917-84-2
• Molecular Formula: C₁₇H₂₄O₆
• Molecular Weight: 324.374
• Mol file: 109917-84-2.mol

Synonyms:4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose

Chemical Property of 4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose

There total 9 articles about 4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose 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: 72.0%

C10H18O6 + benzyl bromide (100-39-0) → 4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose (109917-84-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1021/acschembio.6b00568

Reference yield:

allyl 4-O-benzyl-α-L-rhamnopyranoside (89821-78-3) → 4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose (109917-84-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) tris(triphenylphosphine)rhodium chloride,1,4-diazabicyclo<2.2.2>octane, 2.) HCl, / 1.) reflux, overnight, 2.) acetone, reflux, 1 h,

2: 93 percent / pyridine / 16 h / Ambient temperature

3: (CH₃)3SiBr, / CH₂Cl₂ / 3 h / Ambient temperature

4: 65 percent / various solvent(s) / 51 h

5: NH₃, / methanol / 72 h / Ambient temperature

6: 1.) NaH, / 1.) THF, 0 deg C, 2 h, 2.) THF, RT; overnight,

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; Wilkinson's catalyst; trimethylsilyl bromide; ammonia; sodium hydride; In pyridine; methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90098-3

Reference yield:

1,2,3-tri-O-acetyl-4-O-benzyl-α-L-rhamnopyranose (73983-14-9) → 4-O-benzyl-1,2-O-(1-methoxyethylidene)-3-O-methyl-β-L-rhamnopyranose (109917-84-2)

Guidance literature:

Multi-step reaction with 4 steps

1: (CH₃)3SiBr, / CH₂Cl₂ / 3 h / Ambient temperature

2: 65 percent / various solvent(s) / 51 h

3: NH₃, / methanol / 72 h / Ambient temperature

4: 1.) NaH, / 1.) THF, 0 deg C, 2 h, 2.) THF, RT; overnight,

With trimethylsilyl bromide; ammonia; sodium hydride; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90098-3

upstream raw materials:

(3aR,5S,6R,7R,7aR)-6-Benzyloxy-2-methoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-ol

methyl iodide

allyl 4-O-benzyl-α-L-rhamnopyranoside

1,2,3-tri-O-acetyl-4-O-benzyl-α-L-rhamnopyranose

Downstream raw materials:

8-(methoxycarbonyl)octyl 2-O-acetyl-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

8-(methoxycarbonyl)octyl 4-O-benzyl-2,3-di-O-methyl-α-L-rhamnopyranoside

8-(methoxycarbonyl)octyl 4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside