(1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione

Base Information

• Chemical Name: (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione
• CAS No.: 187961-09-7
• Molecular Formula: C₃₉H₅₈O₈Si
• Molecular Weight: 682.97

Synonyms:(1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione

Chemical Property of (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione

Chemical Property:

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Technology Process of (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione

There total 9 articles about (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione 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:

(1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-7,11,14,14-tetramethyl-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione (187960-89-0) → (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione (187961-09-7)

Guidance literature:

With ammonium fluoride; In methanol; at 20 ℃;

DOI:10.1021/ja963539z

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione (187961-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-diisopropylethylamine / 55 °C

2: NH₄F / methanol / 20 °C

With ammonium fluoride; N-ethyl-N,N-diisopropylamine; In methanol; 1: Etherification / 2: desilylation;

DOI:10.1021/ja963539z

Reference yield:

C29H48O7Si (187960-83-4) → (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione (187961-09-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / tetrahydrofuran / -78 °C

2: 94 percent / HCl; H₂O; NaI / dioxane

3: 92 percent / pyridine / CH₂Cl₂ / -30 °C

4: Dess-Martin periodinane / CH₂Cl₂

5: Et₃N

6: 89 percent / ZnCl₂ / tetrahydrofuran / -78 °C

7: N,N-diisopropylethylamine / 55 °C

8: NH₄F / methanol / 20 °C

With pyridine; hydrogenchloride; ammonium fluoride; water; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1: Wittig reaction / 2: Hydrolysis / 3: silylation / 4: Oxidation / 5: methylenation / 6: Grignard reaction / 7: Etherification / 8: desilylation;

DOI:10.1021/ja963539z

upstream raw materials:

(1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-7,11,14,14-tetramethyl-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione

Benzyloxymethyl chloride

C₂₉H₄₈O₇Si

((1S,5S,6R,7S,8S,9S,12S)-8,9-Dihydroxy-7,11,14,14-tetramethyl-3-oxo-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-en-6-yl)-acetaldehyde

Downstream raw materials:

C₄₂H₅₆BrCl₃O₁₃Si

Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl ester

Benzoic acid (1S,2S,3S,4S,5S,9S)-5-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-pent-4-enyl)-1-hydroxy-4,8,11,11-tetramethyl-6-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-pent-4-enyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

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