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

Base Information

• Chemical Name: Benzoic acid (S)-6-[(R)-4-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 259187-22-9
• Molecular Formula: C₃₅H₅₄O₇Si
• Molecular Weight: 614.895

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

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

Chemical Property:

Purity/Quality:

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

There total 15 articles about Benzoic acid (S)-6-[(R)-4-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-yl 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: 88.0%

Benzoic acid (S)-6-formyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester (259187-21-8) + (2-benzyloxymethoxymethyl-4-iodo-butoxy)-tert-butyl-dimethyl-silane (259187-28-5) → 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)

Guidance literature:

(2-benzyloxymethoxymethyl-4-iodo-butoxy)-tert-butyl-dimethyl-silane; With magnesium;

Benzoic acid (S)-6-formyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester; In diethyl ether; at -78 ℃;

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) → 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)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; dmap; sodium periodate; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; 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;

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 → 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)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; dmap; sodium periodate; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; 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;

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

upstream raw materials:

Benzoic acid (S)-6-formyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester

(2-benzyloxymethoxymethyl-4-iodo-butoxy)-tert-butyl-dimethyl-silane

Benzyloxymethyl chloride

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

Downstream raw materials:

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

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

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