(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

Base Information

Chemical Name:(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
CAS No.:99297-90-2
Molecular Formula:C₃₅H₅₂O₈
Molecular Weight:600.793
Hs Code.:

Synonyms:(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

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Chemical Property of (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

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Technology Process of (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

There total 3 articles about (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-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: 71.0%

: 99285-08-2
(1S,2R,4R,5R,9S,10R,13R,14R,15R,19S,20S)-4,14-Bis-benzyloxy-13-ethyl-2,4,7,7,10,14,17,17,19,20-decamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

: 99297-90-2
(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

Guidance literature:: With acetyl chloride; In methanol; at 25 ℃; for 1.5h;
DOI:10.1139/v85-469

Reference yield:

: 100-39-0
benzyl bromide

: 99297-90-2
(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / NaH / dimethylformamide / 2.5 h / 25 °C

2: 71 percent / acetyl chloride / methanol / 1.5 h / 25 °C

With sodium hydride; acetyl chloride; In methanol; N,N-dimethyl-formamide;
DOI:10.1139/v85-469

Reference yield:

: 99285-07-1
3,5:9,11-di-O-isopropylidene.(9S)-9-deoxo-hydroxyerythronolide

: 99297-90-2
(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-7,13-Bis-benzyloxy-14-ethyl-4,6,10,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / NaH / dimethylformamide / 2.5 h / 25 °C

2: 71 percent / acetyl chloride / methanol / 1.5 h / 25 °C

With sodium hydride; acetyl chloride; In methanol; N,N-dimethyl-formamide;
DOI:10.1139/v85-469