(1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate

Base Information

Chemical Name:(1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate
CAS No.:174709-90-1
Molecular Formula:C₂₄H₄₆O₇Si
Molecular Weight:474.711
Hs Code.:

Synonyms:(1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate

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Chemical Property of (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate

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Technology Process of (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate

There total 8 articles about (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate 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: 70.0%

: 126587-69-7
(3S,4S,5R)-6-<(tert-butyldimethylsilyl)oxy>-4-(methoxymethoxy)-2,5-dimethyl-3-hexanol

: 174709-89-8
(1S,2S)-2-methoxy-3-oxocyclohexanecarbonyl fluoride

: 174709-90-1
(1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate

Guidance literature:: With NaHMSA; In tetrahydrofuran; 1.) -78 deg C, 30 min; 0 deg C, 10 min, 2.) 0 deg C, 10 min; room temperature, 4 h;
DOI:10.1021/jo951693i

Reference yield:

: 158195-44-9
(1S,4S,5S,8S)-4-Iodo-8-methoxy-6-oxa-bicyclo[3.2.1]octan-7-one

: 174709-90-1
(1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / Bu₃SnH, AIBN / benzene

2: 99 percent / LiOH / H₂O; tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 16 h

3: 89 percent / acetone, CrO₃, H₂SO₄ / H₂O / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

4: 99 percent / cyanuric fluoride, pyridine / CH₂Cl₂ / 1 h / -30 - -20 °C

5: 70 percent / NaHMSA / tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 10 min, 2.) 0 deg C, 10 min; room temperature, 4 h

With pyridine; chromium(VI) oxide; lithium hydroxide; trifluoro-[1,3,5]triazine; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; acetone; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1021/jo951693i

Reference yield:

: 158252-23-4
(1S,2R)-2-methoxy-3-cyclohexenyl-1-carboxylic acid

: 174709-90-1
(1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / NaHCO₃, KI, I₂ / H₂O

2: 99 percent / Bu₃SnH, AIBN / benzene

3: 99 percent / LiOH / H₂O; tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 16 h

4: 89 percent / acetone, CrO₃, H₂SO₄ / H₂O / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

5: 99 percent / cyanuric fluoride, pyridine / CH₂Cl₂ / 1 h / -30 - -20 °C

6: 70 percent / NaHMSA / tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 10 min, 2.) 0 deg C, 10 min; room temperature, 4 h

With pyridine; chromium(VI) oxide; lithium hydroxide; trifluoro-[1,3,5]triazine; 2,2'-azobis(isobutyronitrile); sulfuric acid; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; acetone; potassium iodide; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1021/jo951693i