(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

Base Information

Chemical Name:(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one
CAS No.:99300-06-8
Molecular Formula:C₃₈H₅₆O₈
Molecular Weight:640.858
Hs Code.:

(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

Synonyms:(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

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Chemical Property of (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

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Technology Process of (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

There total 4 articles about (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-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: 95.0%

: 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

: 67-64-1
acetone

: 99300-06-8
(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

Guidance literature:: With hydrogenchloride; calcium sulfate; at 0 ℃; for 1h;
DOI:10.1139/v85-469

Reference yield:

: 100-39-0
benzyl bromide

: 99300-06-8
(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 95 percent / HCl, Drierite / 1 h / 0 °C

With hydrogenchloride; calcium sulfate; 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

: 99300-06-8
(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-6,12-Bis-benzyloxy-5-ethyl-7,9-dihydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 95 percent / HCl, Drierite / 1 h / 0 °C

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