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

Base Information

Chemical Name: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
CAS No.:110046-06-5
Molecular Formula:C₃₅H₄₄O₉
Molecular Weight:608.729
Hs Code.:

Synonyms: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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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 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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Technology Process of 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

There total 12 articles about 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 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: 85.0%

: 110045-95-9
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

: 110046-06-5
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

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; for 12h; Ambient temperature;
DOI:10.1021/jo00229a015

Reference yield:

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

: 110046-06-5
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

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.166667h;
DOI:10.1021/jo00229a015

Reference yield:

: 100-39-0
benzyl bromide

: 110046-06-5
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

Guidance literature:: Multi-step reaction with 8 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: 72 percent / diethyl ether / -78 - -60 °C

5: 29 percent / tetrahydrofuran / -78 - 0 °C

6: 4-(dimethylamino)pyridine / ethyl acetate / Ambient temperature

7: 1.) O₃, 2.) Me₂S / 1.) methanol, CH₂Cl₂, RT, 0.5 , 2.) methanol, CH₂Cl₂, RT, 0.5 h

8: NaBH₄ / methanol / 0.17 h / 0 °C

With dmap; sodium tetrahydroborate; florisil; dimethylsulfide; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo00229a015