(2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal

Base Information

Chemical Name:(2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal
CAS No.:326606-22-8
Molecular Formula:C₂₁H₃₃NO₁₀
Molecular Weight:459.494
Hs Code.:

Synonyms:(2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal

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Chemical Property of (2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal

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Technology Process of (2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal

There total 15 articles about (2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal 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: 60.0%

: 326606-21-7
(2R,3S,5R)-3-methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexan-1-ol

: 326606-22-8
(2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate;
DOI:10.1021/ol0068997 DOI:10.1021/jo034870l

Reference yield:

: 326606-26-2
(3S,5S,6S)-3-[(1S,3R)-1-methoxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one

: 326606-22-8
(2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiBH₄

1.2: CAN

2.1: i-Pr₂NEt

3.1: TBAF

4.1: 60 percent / TPAP; NMO

With lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine;
DOI:10.1021/jo034870l

Reference yield:

: 135-77-3
1,2,4-trimethoxy-benzene

: 326606-22-8
(2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal

Guidance literature:: Multi-step reaction with 14 steps

1.1: n-BuLi / diethyl ether; hexane / 2 h / Heating

1.2: 68 percent / diethyl ether; hexane / 2 h / Heating

2.1: 83 percent / HNO₃; AcOH / 0.5 h / 60 °C

3.1: 98 percent / NaBH₄ / tetrahydrofuran / 1 h / 20 °C

4.1: 93 percent / PBr₃; pyridine / diethyl ether / 0.5 h / 20 °C

5.1: 88 percent / NaHMDS / tetrahydrofuran / 3.5 h / -78 °C

6.1: 96 percent / LiBH₄; H₂O / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

7.1: 81 percent / DEAD; PPh₃ / diethyl ether / 20 h / 20 °C

8.1: 92 percent / DIBAL / toluene / -78 - 20 °C

9.1: (c-Hex)2BOTf; Et₃N / CH₂Cl₂; hexane / -78 °C

9.2: 70 percent / CH₂Cl₂; hexane / 3 h / -78 °C

10.1: 91 percent / CH₂Cl₂ / 8 h / 20 °C

11.1: 99 percent / LiBH₄ / tetrahydrofuran; methanol / 0 - 20 °C

12.1: 80 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.5 h / 0 °C

13.1: TBSCl; i-Pr₂NEt; 4-DMAP / CH₂Cl₂ / 32 h

13.2: 77 percent / CH₂Cl₂ / 10 h

14.1: 60 percent / TPAP; NMO

With pyridine; dmap; sodium tetrahydroborate; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ammonium cerium(IV) nitrate; water; nitric acid; sodium hexamethyldisilazane; phosphorus tribromide; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; 5.1: Evan's asymmetric alkylation / 7.1: Mitsunobu reaction;
DOI:10.1021/ol0068997