(2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran
CAS No.:251319-61-6
Molecular Formula:C₂₈H₅₀O₇Si₂
Molecular Weight:554.872
Hs Code.:

(2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

Synonyms:(2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

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Chemical Property of (2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

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Technology Process of (2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

There total 11 articles about (2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran 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: 83.0%

: 321921-84-0
Benzoic acid (1R,2R,3S)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2S,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-1-((R)-1,2-dihydroxy-ethyl)-butyl ester

: 251319-61-6
(2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4039(99)01481-1

Reference yield:

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

: 251319-61-6
(2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

Guidance literature:: Multi-step reaction with 9 steps

1.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran / -78 °C

1.2: diisobutyl aluminium hydride / CH₂Cl₂ / -78 °C

2.1: imidazole / dimethylformamide / 20 °C

3.1: 97 percent / di-tert-butyldiphenyllithium / tetrahydrofuran / -78 °C

4.1: 82 percent / (-)-diethyl tartrate; 4 Angstroem molecular sieves; tBuOOH / Ti(iPrO)4 / CH₂Cl₂ / -20 °C

5.1: 80 percent / Ti(iPrO)4 / tetrahydrofuran / 20 °C

6.1: 99 percent / Et₃N / CH₂Cl₂ / 20 °C

7.1: 99 percent / dimethyl dioxirane / CH₂Cl₂ / -20 °C

8.1: camphorsulfonic acid / CH₂Cl₂; methanol / -20 °C

9.1: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; potassium hexamethylsilazane; lithium 4,4′-di-tert-butylbiphenylide; (-)-diethyl tartrate; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Alkylation / 1.2: Reduction / 2.1: silylation / 3.1: Hydrolysis / 4.1: Epoxidation / 5.1: benzoylation / 6.1: silylation / 7.1: Epoxidation / 8.1: Hydrolysis / 9.1: Cyclization;
DOI:10.1016/S0040-4039(99)01481-1

Reference yield:

: 321921-91-9
(2Z,6E)-(4S,5S)-8-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-octa-2,6-dien-1-ol

: 251319-61-6
(2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 20 °C

2: 97 percent / di-tert-butyldiphenyllithium / tetrahydrofuran / -78 °C

3: 82 percent / (-)-diethyl tartrate; 4 Angstroem molecular sieves; tBuOOH / Ti(iPrO)4 / CH₂Cl₂ / -20 °C

4: 80 percent / Ti(iPrO)4 / tetrahydrofuran / 20 °C

5: 99 percent / Et₃N / CH₂Cl₂ / 20 °C

6: 99 percent / dimethyl dioxirane / CH₂Cl₂ / -20 °C

7: camphorsulfonic acid / CH₂Cl₂; methanol / -20 °C

8: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; lithium 4,4′-di-tert-butylbiphenylide; (-)-diethyl tartrate; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Hydrolysis / 3: Epoxidation / 4: benzoylation / 5: silylation / 6: Epoxidation / 7: Hydrolysis / 8: Cyclization;
DOI:10.1016/S0040-4039(99)01481-1