(3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

Base Information

Chemical Name:(3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one
CAS No.:157427-43-5
Molecular Formula:C₃₃H₄₈O₆
Molecular Weight:540.741
Hs Code.:

Synonyms:(3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

Chemical Property:

Purity/Quality:: 99% ^*data from raw suppliers

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Technology Process of (3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

There total 19 articles about (3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-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: 63.0%

: 157427-37-7
(S)-6-((2S,4R,6S)-4-Methoxy-6-methyl-tetrahydro-pyran-2-yl)-4-methyl-hexan-3-one

: 157427-38-8
(2S,3S)-3,4-Bis-benzyloxy-2-methyl-butyraldehyde

: 157427-43-5
(3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

Guidance literature:: With titanium tetrachloride; triethylamine; In dichloromethane; at -78 ℃; for 8h;
DOI:10.1039/c39940001151

Reference yield:

: 59983-36-7
(S)-1-(1-Ethylpropylidenamino)-2-methoxymethylpyrrolidin

: 157427-43-5
(3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA / 1.) Et₂O, hexane, 0 deg C, 4 h, 2.) Et₂O, hexane, from -110 deg C to RT, 12 h

2: 97 percent / O₃ / CH₂Cl₂ / -78 °C

3: 1.) TiCl₄, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 2.5 h

With titanium tetrachloride; ozone; triethylamine; lithium diisopropyl amide; In dichloromethane;

Reference yield:

: (2S,3S,4R,5S,6S)-2-Allyl-4-methoxy-6-methyl-tetrahydro-pyran-3,5-diol

: 157427-43-5
(3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) imidazole, NaH

2: 60 percent / n-Bu₃SnH, AIBN / toluene / 1 h / 110 °C

3: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 20 min, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT, 7 h

4: 83 percent / Ph₃P, I₂, imidazole / CH₂Cl₂ / 2 h / 40 °C

5: 1.) LDA / 1.) Et₂O, hexane, 0 deg C, 4 h, 2.) Et₂O, hexane, from -110 deg C to RT, 12 h

6: 97 percent / O₃ / CH₂Cl₂ / -78 °C

7: 1.) TiCl₄, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 2.5 h

With 1H-imidazole; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; titanium tetrachloride; sodium hydride; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide; In dichloromethane; toluene;