3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid

Base Information

Chemical Name:3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid
CAS No.:170706-78-2
Molecular Formula:C₃₂H₄₈O₆Si
Molecular Weight:556.815
Hs Code.:

Synonyms:3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid

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Chemical Property of 3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid

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Technology Process of 3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid

There total 11 articles about 3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid 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: 94.0%

: 170706-77-1
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid methyl ester

: 170706-78-2
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; at 55 ℃; for 2.5h;
DOI:10.1021/ja00146a008

Reference yield:

: 131311-02-9
(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 170706-78-2
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

2: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1 h, 2.) THF, 0 deg C, 1 h

3: 88 percent / KH / tetrahydrofuran / 1 h / 45 °C

4: 89 percent / CSA / methanol / 1 h / 0 °C

5: 95 percent / imidazole / dimethylformamide / 14 h / 45 °C

6: 89 percent / CSA / methanol / 1 h / 0 °C

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

8: benzene / 12 h / 50 °C

9: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 25 °C

10: 94 percent / aq. LiOH / tetrahydrofuran; methanol / 2.5 h / 55 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; potassium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00146a008

Reference yield:

: 100-39-0
benzyl bromide

: 170706-78-2
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-propionic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

2: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1 h, 2.) THF, 0 deg C, 1 h

3: 88 percent / KH / tetrahydrofuran / 1 h / 45 °C

4: 89 percent / CSA / methanol / 1 h / 0 °C

5: 95 percent / imidazole / dimethylformamide / 14 h / 45 °C

6: 89 percent / CSA / methanol / 1 h / 0 °C

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

8: benzene / 12 h / 50 °C

9: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 25 °C

10: 94 percent / aq. LiOH / tetrahydrofuran; methanol / 2.5 h / 55 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; potassium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00146a008