(3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

Base Information

Chemical Name:(3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone
CAS No.:262375-68-8
Molecular Formula:C₂₄H₃₆O₄
Molecular Weight:388.547
Hs Code.:

Synonyms:(3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

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Chemical Property of (3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

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Technology Process of (3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

There total 15 articles about (3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone 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:

: 98-86-2
acetophenone

: 2-Methyl-2-[(4R,5R,6S)-2,2,5-trimethyl-6-((S)-1-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-propionaldehyde

: (R)-3-Hydroxy-4-methyl-1-phenyl-4-[(4R,5R,6S)-2,2,5-trimethyl-6-((S)-1-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-pentan-1-one

: 262375-68-8
(3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

: (R)-3-Hydroxy-4-methyl-1-phenyl-4-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-pentan-1-one

: (3S,4'S,5'S,6'R,4''R)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

Guidance literature:: With (R)-[LaLi₃{tris(binaphthoxide)}]; water; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -20 ℃; for 168h; Title compound not separated from byproducts;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield:

: 2-Methyl-2-[(4R,5R,6S)-2,2,5-trimethyl-6-((S)-1-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-propan-1-ol

: 262375-68-8
(3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / TPAP; NMO; molecular sieves 4 A / CH₂Cl₂

2.1: potassium bis(trimethylsilyl)amide; H₂O / (R)-LaLi₃tris(binaphthoxide) / toluene; tetrahydrofuran / 0.33 h / -20 °C

2.2: toluene; H₂O; tetrahydrofuran / 168 h / -20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; water; potassium hexamethylsilazane; (R)-LaLi₃tris(binaphthoxide); In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja002024b

Reference yield:

: (4S,5R)-7-Benzyloxy-5-hydroxy-4,6,6-trimethyl-heptan-3-one

: 262375-68-8
(3S,4'R,5'R,6'S,4''S)-3-hydroxy-4-methyl-4-[2,2,5-trimethyl-6-(1-pente-4-yl)-1,3-dioxan-4-yl]pentophenone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; LHMDS / tetrahydrofuran / 0.67 h / -78 °C

1.2: 48 percent / tetrahydrofuran / 1.5 h / -78 °C

2.1: 79 percent / Me₄NBH(OAc)3; AcOH / acetonitrile

3.1: 96 percent / TsOH / dimethylformamide

4.1: 100 percent / Li; liq. NH₃ / 2-methyl-propan-2-ol; tetrahydrofuran

5.1: 89 percent / TPAP; NMO; molecular sieves 4 A / CH₂Cl₂

6.1: potassium bis(trimethylsilyl)amide; H₂O / (R)-LaLi₃tris(binaphthoxide) / toluene; tetrahydrofuran / 0.33 h / -20 °C

6.2: toluene; H₂O; tetrahydrofuran / 168 h / -20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; ammonia; water; lithium; potassium hexamethylsilazane; toluene-4-sulfonic acid; acetic acid; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; (R)-LaLi₃tris(binaphthoxide); In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 4.1: Birch reduction;
DOI:10.1021/ja002024b