methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside

Base Information

• Chemical Name: methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside
• CAS No.: 110045-95-9
• Molecular Formula: C₃₅H₄₂O₇
• Molecular Weight: 574.714

Synonyms:methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside

Chemical Property of methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside

There total 7 articles about methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside 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:

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-butyl)-6-methoxy-tetrahydro-pyran-3-yl ester → methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside (110045-95-9)

Guidance literature:

With thionyl chloride; In pyridine; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo00229a015

Reference yield:

benzyl bromide (100-39-0) → methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside (110045-95-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) DMF, 0 deg C, 20 min, 2.) DMF, RT, 45 min

2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; dioxane; H₂O / 4 h / Ambient temperature

3: pyridinium chlorochromate (PCC), Celite, Florisil, sodium acetate / CH₂Cl₂ / Ambient temperature

4: tetrahydrofuran / 1 h / Ambient temperature

5: pyridine / 16 h / 40 °C

6: thionyl chloride / pyridine / 0.08 h / 0 °C

With pyridine; florisil; thionyl chloride; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water;

DOI:10.1021/jo00229a015

Reference yield:

methyl-(1) 3,4-dimethoxybenzyl-(8)(8R)-2,3-di-O-benzyl-6-deoxy-6-C-methyl-β-L-threo-D-gluco-octodialdo-1,5:8,4-dipyranoside (110045-79-9) → methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside (110045-95-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) DMF, 0 deg C, 20 min, 2.) DMF, RT, 45 min

2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; dioxane; H₂O / 4 h / Ambient temperature

3: pyridinium chlorochromate (PCC), Celite, Florisil, sodium acetate / CH₂Cl₂ / Ambient temperature

4: tetrahydrofuran / 1 h / Ambient temperature

5: pyridine / 16 h / 40 °C

6: thionyl chloride / pyridine / 0.08 h / 0 °C

With pyridine; florisil; thionyl chloride; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water;

DOI:10.1021/jo00229a015

upstream raw materials:

benzyl bromide

methyl-(1) 3,4-dimethoxybenzyl-(8)(8R)-2,3-di-O-benzyl-6-deoxy-6-C-methyl-β-L-threo-D-gluco-octodialdo-1,5:8,4-dipyranoside

methyl 2,3,7-tri-O-benzyl-6-deoxy-6-C-methyl-L-threo-α-D-gluco-octapyranosiduronic acid γ-lactone

(2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran

Downstream raw materials:

methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6-deoxy-6,8-di-C-methyl-L-arabino-α-D-gluco-nono-1,5-pyranoside

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