methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside

Base Information

• Chemical Name: methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside
• CAS No.: 110045-99-3
• Molecular Formula: C₃₃H₃₈O₈
• Molecular Weight: 562.66

Synonyms:methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside

Chemical Property of methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside

There total 9 articles about methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-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: 92.0%

methyl 4-O-benzoyl-2,3-di-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-7-O-(tert-butyldimethylsilyl)-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside (110045-94-8) → methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside (110045-99-3)

Guidance literature:

With tert.-butylhydroperoxide; vanadyl acetylacetonate; In 1,2-dichloro-ethane; benzene; for 0.5h; Ambient temperature;

DOI:10.1021/jo00229a015

Reference yield:

benzoyl chloride (98-88-4) → methyl 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside (110045-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 16 h / 40 °C

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

3: dl-camphorsulfonic acid / methanol / 20 h / Ambient temperature

4: 92 percent / tert-butyl hydroperoxide, vanadyl acetylacetonate / benzene; 1,2-dichloro-ethane / 0.5 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; thionyl chloride; vanadyl acetylacetonate; camphor-10-sulfonic acid; In pyridine; methanol; 1,2-dichloro-ethane; benzene;

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 8,9-anhydro-4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-C-arabino-α-D-gluco-nono-1,5-pyranoside (110045-99-3)

Guidance literature:

Multi-step reaction with 8 steps

1: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

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

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

4: 94 percent / tetrahydrofuran / 1 h / Ambient temperature

5: pyridine / 16 h / 40 °C

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

7: dl-camphorsulfonic acid / methanol / 20 h / Ambient temperature

8: 92 percent / tert-butyl hydroperoxide, vanadyl acetylacetonate / benzene; 1,2-dichloro-ethane / 0.5 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; dmap; florisil; thionyl chloride; Celite; vanadyl acetylacetonate; camphor-10-sulfonic acid; sodium acetate; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; 1,2-dichloro-ethane; benzene;

DOI:10.1021/jo00229a015

upstream raw materials:

methyl 4-O-benzoyl-2,3-di-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-7-O-(tert-butyldimethylsilyl)-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside

benzoyl chloride

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

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1,3-dimethyl-butyl]-6-methoxy-tetrahydro-pyran-3-ol

Downstream raw materials:

Phenyl-carbamic acid (3R,4S,5R)-5-((E)-(S)-1,3-bis-benzyloxy-4-oxo-but-2-enyl)-2-hydroxymethyl-2,4-dimethyl-tetrahydro-furan-3-yl ester

Benzoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-[(S)-1-((4R,5R)-5-hydroxymethyl-5-methyl-2-oxo-[1,3]dioxolan-4-yl)-ethyl]-6-methoxy-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2,4-diacetoxy-3-hydroxy-1,3-dimethyl-butyl)-6-methoxy-tetrahydro-pyran-3-yl ester

methyl 2,3-di-O-benzyl-6-deoxy-6,8-di-C-methyl-D-xylo-α-D-gluco-nono-1,5-pyranoside

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