(2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal

Base Information

Chemical Name:(2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal
CAS No.:1309595-63-8
Molecular Formula:C₂₈H₅₂O₄Si₂
Molecular Weight:508.889
Hs Code.:

Synonyms:(2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal

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Chemical Property of (2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal

Chemical Property:

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Technology Process of (2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal

There total 7 articles about (2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal 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: 83.0%

: 1309595-62-7
(3R,4S,6R)-9-(benzyloxy)-4,6-bis((tert-butyldimethylsilyl)oxy)-3-methylnon-1-ene

: 1309595-63-8
(2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal

Guidance literature:: (3R,4S,6R)-9-(benzyloxy)-4,6-bis((tert-butyldimethylsilyl)oxy)-3-methylnon-1-ene; With pyridine; ozone; In methanol; dichloromethane; at -78 ℃; for 0.333333h;

With dimethylsulfide; oxygen; In methanol; dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo200466t

Reference yield:

: 1309595-60-5
(R)-6-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)hexanal

: 1309595-63-8
(2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal

Guidance literature:: Multi-step reaction with 3 steps

1.1: (4S,5S)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O^α)titanium / tetrahydrofuran; diethyl ether / 3 h / 0 °C

1.2: 0.33 h / -78 °C

1.3: 12 h / 20 °C

2.1: triethylamine / dichloromethane / 1 h / -78 °C

3.1: pyridine; ozone / methanol; dichloromethane / 0.33 h / -78 °C

3.2: -78 - 20 °C

With pyridine; (4S,5S)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O^α)titanium; ozone; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jo200466t

Reference yield:

: 1309595-61-6
(3R,4S,6R)-9-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)-3-methylnon-1-en-4-ol

: 1309595-63-8
(2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 1 h / -78 °C

2.1: pyridine; ozone / methanol; dichloromethane / 0.33 h / -78 °C

2.2: -78 - 20 °C

With pyridine; ozone; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jo200466t