(2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one

Base Information

• Chemical Name: (2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one
• CAS No.: 133814-76-3
• Molecular Formula: C₄₆H₆₄O₇
• Molecular Weight: 729.01
• Mol file: 133814-76-3.mol

Synonyms:

Chemical Property of (2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one

There total 1 articles about (2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-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:

(4R,6R)-6-Benzyloxy-4-methyl-6-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-heptan-3-one (114114-23-7) + 4,5-didesoxy-2,3-di-O-benzyl-2-C-methyl-D-threoaldehydopentose (85433-10-9) → (2R,4R,6R,7R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one (133782-38-4) + (2R,4R,6S,7S,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one (133814-76-3)

Guidance literature:

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, hexane, 3 h, -60 deg C 2) THF, 15 min, -78 deg C;

DOI:10.1016/S0040-4020(01)96140-X

Reference yield:

(2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one (133782-38-4,133814-76-3) → (2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecane-5,7-diol

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In diethyl ether; for 1h; Yield given;

DOI:10.1016/S0040-4020(01)96140-X

Reference yield:

(2R,4R,8S,9R)-2,8,9-Tris-benzyloxy-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one (133782-38-4,133814-76-3) → Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester (133782-40-8)

Guidance literature:

Multi-step reaction with 9 steps

1: LiAlH(t-BuO)3 / diethyl ether / 1 h

2: DMP, (+/-)-10-camphorosulfonic acid / 0.25 h / Ambient temperature

3: 100 percent / Na, NH₃ / diethyl ether / 1 h / -78 °C

4: O₃, pyridine / CH₂Cl₂ / -78 °C

5: m-CPBA / tetrahydrofuran / 0.5 h / 20 °C

6: 68 percent / 2,2-dithio-bis(4-t-butyl-1-isopropylimidazole), PPh₃ / toluene / 20 h / Heating

7: 95 percent / LiAlH₄ / diethyl ether / 1.5 h / -50 deg C to r.t.

8: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

9: EtN₃ / CH₂Cl₂ / 0.25 h / -20 - 20 °C

With pyridine; lithium aluminium tetrahydride; phthalic acid dimethyl ester; 10-camphorsufonic acid; ammonia; sodium; ozone; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; bis(4-tert-butyl-1-iso-propyl-1H-imidazol-2-yl)disulfide; ethyl azide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)96140-X

upstream raw materials:

(4R,6R)-6-Benzyloxy-4-methyl-6-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-heptan-3-one

4,5-didesoxy-2,3-di-O-benzyl-2-C-methyl-D-threoaldehydopentose

Downstream raw materials:

Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester

C₄₉H₇₀O₇

C₄₉H₇₀O₇