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

Base Information

• Chemical Name: (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one
• CAS No.: 259187-23-0
• Molecular Formula: C₂₈H₄₆O₆Si
• Molecular Weight: 506.755

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 17 articles about (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one 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%

(S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol (259187-30-9) → (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one (259187-23-0)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; 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)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one (259187-23-0)

Guidance literature:

Multi-step reaction with 9 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

9.1: 96 percent / TPAP; NMO; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

With pyridine; methanol; dmap; sodium periodate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; 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 / 9.1: Oxidation;

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)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one (259187-23-0)

Guidance literature:

Multi-step reaction with 8 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

8.1: 96 percent / TPAP; NMO; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

With pyridine; methanol; dmap; sodium periodate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; 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 / 8.1: Oxidation;

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

upstream raw materials:

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

Benzyloxymethyl chloride

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

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

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