(10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one

Base Information

Chemical Name:(10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one
CAS No.:122592-28-3
Molecular Formula:C₂₂H₂₈O₅
Molecular Weight:372.461
Hs Code.:

Synonyms:(10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one

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Chemical Property of (10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one

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Technology Process of (10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one

There total 31 articles about (10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one 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: 81.0%

: 132548-39-1
C₂₂H₂₇IO₅

: 122592-28-3,132618-85-0
(2aR,3S,4aR,7R,8aS,8bS,11S,11aS)-3-Methoxy-2a,11-dimethyl-7-phenyl-octahydro-4,6,8-trioxa-pentaleno[6a,1-a]naphthalen-10-one

Guidance literature:: With tri-n-butyl-tin hydride; In benzene;
DOI:10.1039/c39900001440

Reference yield: 73.0%

: 122622-29-1
methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside

: 122592-28-3
(10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 1h; Heating;
DOI:10.1021/jo00283a034

Reference yield:

: 122622-39-3
(2R,4aR,6S,7R,8S,8aR)-7-(2-Hydroxy-ethyl)-6-methoxy-7-methyl-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 122592-28-3
(10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one

Guidance literature:: Multi-step reaction with 15 steps

1: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

2: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

3: dimethylformamide / 2 h / 100 °C

4: NaOMe / methanol / Ambient temperature

5: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

6: tetrahydrofuran / 0.17 h

7: Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature

8: MeLi / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

9: mercuric trifluoroacetate / Ambient temperature

10: xylene / 24 h / Heating

11: hydroxylamine hydrochloride, pyridine

12: trifluoroacetic anhydride, pyridine / CH₂Cl₂ / Ambient temperature

13: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

14: iodine, triphenyl phosphine, imidazole / benzene / 0.08 h / Ambient temperature

15: 73 percent / tri-n-butyltin hydride, AIBN / benzene / 1 h / Heating

With pyridine; 1H-imidazole; thionyl chloride; 2,2'-azobis(isobutyronitrile); Celite; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; methyllithium; iodine; tri-n-butyl-tin hydride; sodium methylate; sodium acetate; mercury(II) trifluoroacetate; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; xylene; benzene;
DOI:10.1021/jo00283a034