(2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol

Base Information

• Chemical Name: (2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol
• CAS No.: 173044-02-5
• Molecular Formula: C₃₃H₆₀O₅Si
• Molecular Weight: 564.922

Synonyms:

Chemical Property of (2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol

There total 10 articles about (2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol 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:

Methanesulfonic acid (1S,2S,4S,5S,6S)-1-[(1R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2,5-dihydroxy-6-hydroxymethyl-2,4-dimethyl-octyl ester → (2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol (173044-02-5)

Guidance literature:

With potassium carbonate; In methanol; Ambient temperature;

DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,2-dioxan-4-yl>propan-1-ol (152934-39-9) → (2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol (173044-02-5)

Guidance literature:

Multi-step reaction with 9 steps

2: 1.) t-BuLi / 1.) ether, -78 deg C

3: Swern oxidation

4: diethyl ether / -78 to -20 deg C

5: DDQ / CH₂Cl₂; H₂O / Ambient temperature

6: LiAlH₄ / diethyl ether / 0 °C

7: pyridine / 0 °C

8: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

9: K₂CO₃ / methanol / Ambient temperature

With pyridine; lithium aluminium tetrahydride; sulfuric acid; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane (144534-92-9) → (2S,3S,4S)-5-{(2R,3R)-3-[(1R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1-methyl-hexyl]-2-methyl-oxiranyl}-2-ethyl-4-methyl-pentane-1,3-diol (173044-02-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) t-BuLi / 1.) ether, -78 deg C

2: Swern oxidation

3: diethyl ether / -78 to -20 deg C

4: DDQ / CH₂Cl₂; H₂O / Ambient temperature

5: LiAlH₄ / diethyl ether / 0 °C

6: pyridine / 0 °C

7: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

8: K₂CO₃ / methanol / Ambient temperature

With pyridine; lithium aluminium tetrahydride; sulfuric acid; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(00)61140-1

upstream raw materials:

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,2-dioxan-4-yl>propan-1-ol

(2S,3R,5R,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-2-(4-methoxy-benzyloxy)-3-methyl-octanal

Methanesulfonic acid (1S,2R,4R,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4-ethyl-1-[(1S,3S)-3-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-1-hydroxy-1-methyl-butyl]-2-methyl-heptyl ester

Downstream raw materials:

(1R,2R,4R,5S)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-hydroxymethyl-propyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptan-1-ol

((2S,3R,5S,6S)-6-{(1S,2R,3S,5R)-5-[(2S,4S,5S,2'R,3'R,5'R)-5'-Ethyl-2'-hydroxy-5'-((S)-1-hydroxy-propyl)-2,4,3'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-2-hydroxy-1,3-dimethyl-4-oxo-heptyl}-2-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid

((2S,3R,5S,6S)-6-{(1S,2S,3R,5R)-5-[(2S,4S,5S,2'R,3'R,5'R)-5'-Ethyl-2'-hydroxy-5'-((S)-1-hydroxy-propyl)-2,4,3'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-2-hydroxy-1,3-dimethyl-4-oxo-heptyl}-2-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid

((2S,3R,5S,6S)-6-{(1S,2R,3R,5R)-5-[(2S,4S,5S,2'R,3'R,5'R)-5'-Ethyl-2'-hydroxy-5'-((S)-1-hydroxy-propyl)-2,4,3'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-2-hydroxy-1,3-dimethyl-4-oxo-heptyl}-2-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid

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