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

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 methyl ester
CAS No.:170706-77-1
Molecular Formula:C₃₃H₅₀O₆Si
Molecular Weight:570.842
Hs Code.:

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

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 methyl ester

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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 methyl ester

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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 methyl ester

There total 10 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 methyl ester 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: 100.0%

: 170706-76-0
(E)-3-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

: 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

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 25 ℃; for 6h;
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

: 170706-77-1
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

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; 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

: 170706-77-1
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

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; 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