Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate

Base Information

Chemical Name:Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate
CAS No.:122821-97-0
Molecular Formula:C₃₆H₄₆O₇Si
Molecular Weight:618.843
Hs Code.:

Synonyms:Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate

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Chemical Property of Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate

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Technology Process of Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate

There total 8 articles about Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate 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%

: 122821-96-9
Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-glycero-L-allo-4-undeculosonate

: 122821-97-0
Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.166667h;
DOI:10.1021/ja00199a031

Reference yield:

: 122821-89-0
[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-acetaldehyde

: 122821-97-0
Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / 0.5 h / 0 °C

2: 85 percent / CH₂Cl₂ / 0.17 h / 0 °C

3: 1.) ozone, 2.) dimethylsulfide, triphenylphosphine / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) 3 h

4: benzene / 6 h / 25 °C

5: 72 percent / sodium hydride / tetrahydrofuran / 5 h / 25 °C

6: 69 percent / Jones' reagent / acetone / 0.5 h / 0 °C

7: 85 percent / sodium borohydride / methanol / 0.17 h / 0 °C

With sodium tetrahydroborate; jones' reagent; dimethylsulfide; sodium hydride; ozone; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; acetone; benzene;
DOI:10.1021/ja00199a031

Reference yield:

: 122821-92-5
5,9-Anhydro-7-O-benzyl-10-O-(tert-butyldiphenylsilyl)-1,2,4,8-tetradeoxy-6-C-methyl-3-O-(trimethylsilyl)-D-glycero-L-altro-dec-1-enitol

: 122821-97-0
Methyl 3,7:6,10-anhydro-8-O-benzyl-11-O-(tert-butyldiphenylsilyl)-2,5,9-trideoxy-7-C-methyl-D-threo-L-allo-4-undeculosonate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) ozone, 2.) dimethylsulfide, triphenylphosphine / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) 3 h

2: benzene / 6 h / 25 °C

3: 72 percent / sodium hydride / tetrahydrofuran / 5 h / 25 °C

4: 69 percent / Jones' reagent / acetone / 0.5 h / 0 °C

5: 85 percent / sodium borohydride / methanol / 0.17 h / 0 °C

With sodium tetrahydroborate; jones' reagent; dimethylsulfide; sodium hydride; ozone; triphenylphosphine; In tetrahydrofuran; methanol; acetone; benzene;
DOI:10.1021/ja00199a031