(S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol
• CAS No.: 259187-30-9
• Molecular Formula: C₂₈H₅₀O₆Si
• Molecular Weight: 510.787

Synonyms:(S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol

Chemical Property of (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol

There total 16 articles about (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol 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: 96.0%

Benzoic acid (S)-6-[(R)-4-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester (259187-22-9) → (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol (259187-30-9)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃;

DOI:10.1002/(sici)1521-3773(19991216)38:24<3664::aid-anie3664>3.0.co;2-q

Reference yield:

(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol (50727-94-1,62777-72-4,62960-04-7,71030-55-2,76985-26-7,82188-73-6,112456-40-3,112456-65-2,62777-71-3) → (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol (259187-30-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / NEt₃ / CH₂Cl₂ / -20 - 20 °C

2.1: NMO; C₅H₅N; tert-C₄H₉OH / OsO₄ / tetrahydrofuran / 20 °C

3.1: DCC; DMAP / CH₂Cl₂ / 20 °C

4.1: 88 percent / CSA / CH₂Cl₂ / -15 - 20 °C

5.1: TBAF / tetrahydrofuran / 20 °C

6.1: NaIO₄; H₂O / tetrahydrofuran / 0 °C

7.1: Mg

7.2: 88 percent / diethyl ether / -78 °C

8.1: 96 percent / K₂CO₃; MeOH / 20 °C

With pyridine; methanol; dmap; sodium periodate; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; potassium carbonate; magnesium; triethylamine; dicyclohexyl-carbodiimide; tert-butyl alcohol; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; 1.1: Etherification / 2.1: Oxidation / 3.1: Esterification / 4.1: Ring cleavage / 5.1: Desilylation / 6.1: Oxidation / 7.1: Metallation / 7.2: Grignard reaction / 8.1: Methanolysis;

DOI:10.1002/(sici)1521-3773(19991216)38:24<3664::aid-anie3664>3.0.co;2-q

Reference yield:

(2R,3R)-1-(tert-butyldiphenylsilyloxy)-2,3-epoxy-3,7-dimethyl-6-octene → (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol (259187-30-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NMO; C₅H₅N; tert-C₄H₉OH / OsO₄ / tetrahydrofuran / 20 °C

2.1: DCC; DMAP / CH₂Cl₂ / 20 °C

3.1: 88 percent / CSA / CH₂Cl₂ / -15 - 20 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: NaIO₄; H₂O / tetrahydrofuran / 0 °C

6.1: Mg

6.2: 88 percent / diethyl ether / -78 °C

7.1: 96 percent / K₂CO₃; MeOH / 20 °C

With pyridine; methanol; dmap; sodium periodate; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; potassium carbonate; magnesium; dicyclohexyl-carbodiimide; tert-butyl alcohol; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; 1.1: Oxidation / 2.1: Esterification / 3.1: Ring cleavage / 4.1: Desilylation / 5.1: Oxidation / 6.1: Metallation / 6.2: Grignard reaction / 7.1: Methanolysis;

DOI:10.1002/(sici)1521-3773(19991216)38:24<3664::aid-anie3664>3.0.co;2-q

upstream raw materials:

Benzoic acid (S)-6-[(R)-4-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester

Benzyloxymethyl chloride

(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol

R-(+)-2-(hydroxymethyl)-4-pentenyl acetate

Downstream raw materials:

(S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one

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