(2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one

Base Information

Chemical Name:(2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one
CAS No.:1610702-33-4
Molecular Formula:C₄₂H₅₂O₁₀
Molecular Weight:716.869
Hs Code.:

Synonyms:(2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one

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Chemical Property of (2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one

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Technology Process of (2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one

There total 10 articles about (2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-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: 91.0%

: 1610702-32-3
(2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyloctan-3-one

: 1610702-33-4
(2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one

Guidance literature:: With methanesulfonamide; AD-mix α; potassium carbonate; In water; tert-butyl alcohol; at 0 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo5008527

Reference yield:

: 3,5-bis((benzyloxy)methoxy)-4-bromo-1-prop-1-en-1-ylbenzene

: 1610702-33-4
(2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) / toluene / 24 h / Reflux; Inert atmosphere

2.1: potassium carbonate; palladium diacetate; ruphos / water; toluene / 1.5 h / 85 °C / Inert atmosphere

3.1: methyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

5.1: boron trifluoride diethyl etherate / dichloromethane / 0.03 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 °C / Inert atmosphere

6.1: methanesulfonamide; AD-mix α; potassium carbonate / water; tert-butyl alcohol / 16 h / 0 °C / Inert atmosphere

With dmap; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); methanesulfonamide; boron trifluoride diethyl etherate; AD-mix α; methyllithium; palladium diacetate; potassium carbonate; triethylamine; ruphos; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 2.1: |Suzuki Coupling / 5.1: |Mukaiyama Aldol Addition / 5.2: |Mukaiyama Aldol Addition;
DOI:10.1021/jo5008527

Reference yield:

: 1450741-59-9
(S,E)-4-(2,6-bis((benzyloxy)methoxy)-4-(prop-1-en-1-yl)phenyl)-3-methylbutan-2-one

: 1610702-33-4
(2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.03 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

3.1: methanesulfonamide; AD-mix α; potassium carbonate / water; tert-butyl alcohol / 16 h / 0 °C / Inert atmosphere

With dmap; methanesulfonamide; boron trifluoride diethyl etherate; AD-mix α; potassium carbonate; triethylamine; In dichloromethane; water; tert-butyl alcohol; 2.1: |Mukaiyama Aldol Addition / 2.2: |Mukaiyama Aldol Addition;
DOI:10.1021/jo5008527