(1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

Base Information

Chemical Name:(1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione
CAS No.:1262295-43-1
Molecular Formula:C₄₀H₅₆O₈
Molecular Weight:664.88
Hs Code.:

Synonyms:(1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

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Chemical Property of (1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

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Technology Process of (1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

There total 16 articles about (1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-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: 48.0%

: 1262295-42-0
[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid

: 1262295-43-1
(1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

Guidance literature:: [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 7h; Inert atmosphere;

With dmap; In tetrahydrofuran; toluene; at 125 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jo101782q

Reference yield:

: 1262295-46-4
[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

: 1262295-43-1
(1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 - 60 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: toluene / 48 h / Reflux; Inert atmosphere

4.1: toluene-4-sulfonic acid / chloroform / 20 h / Reflux; Inert atmosphere

5.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 7 h / 20 °C / Inert atmosphere

6.2: 4 h / 125 °C / Inert atmosphere

With oxalyl dichloride; lithium hydroxide monohydrate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Horner-Wittig reaction / 4.1: oxa-Michael cyclization / 6.1: Yamaguchi's lactonization / 6.2: Yamaguchi's lactonization;
DOI:10.1021/jo101782q

Reference yield:

: 1262295-41-9
(E)-(S)-5-benzyloxy-6-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-4,4-dimethyl-hex-2-enoic acid ethyl ester

: 1262295-43-1
(1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / chloroform / 20 h / Reflux; Inert atmosphere

2.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 7 h / 20 °C / Inert atmosphere

3.2: 4 h / 125 °C / Inert atmosphere

With lithium hydroxide monohydrate; 2,4,6-trichlorobenzoyl chloride; water; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; chloroform; 1.1: oxa-Michael cyclization / 3.1: Yamaguchi's lactonization / 3.2: Yamaguchi's lactonization;
DOI:10.1021/jo101782q