(2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran
• CAS No.: 934237-11-3
• Molecular Formula: C₂₇H₄₄O₆
• Molecular Weight: 464.643
• Mol file: 934237-11-3.mol

Synonyms:(2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

Chemical Property of (2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

There total 14 articles about (2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran 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: 90.0%

(2S,3S,6S)-6-[(2S,3S,6R)-(6-methoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)]-2-methylheptan-3-ol (924286-15-7) + ethyl vinyl ether (109-92-2,25104-37-4) → (2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran (934237-11-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.3987/com-06-s(w)13

Reference yield:

(R)-2-[(S)-1-(4-methoxybenzyloxy)propan-2-yl]oxirane (924286-05-5) → (2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran (934237-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

1.2: (2-Th)CuCNLi / diethyl ether; pentane; tetrahydrofuran / 0.08 h / -78 - 0 °C

1.3: 1.16 g / diethyl ether; pentane; tetrahydrofuran / 1 h / 0 °C

2.1: 90 percent / PPTS / CH₂Cl₂ / 1 h / 25 °C

With tert.-butyl lithium; pyridinium p-toluenesulfonate; In diethyl ether; dichloromethane; pentane;

DOI:10.1021/ja066477d

Reference yield:

(2R,5S,6S)-6-[(1S)-2-(p-toluenesulfonyl)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran (924286-08-8) → (2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran (934237-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / NaI / acetone / 12 h / 56 °C

2.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

2.2: (2-Th)CuCNLi / diethyl ether; pentane; tetrahydrofuran / 0.08 h / -78 - 0 °C

2.3: 1.16 g / diethyl ether; pentane; tetrahydrofuran / 1 h / 0 °C

3.1: 90 percent / PPTS / CH₂Cl₂ / 1 h / 25 °C

With tert.-butyl lithium; sodium iodide; pyridinium p-toluenesulfonate; In diethyl ether; dichloromethane; acetone; pentane;

DOI:10.1021/ja066477d

upstream raw materials:

(2S,3S,6S)-6-[(2S,3S,6R)-(6-methoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)]-2-methylheptan-3-ol

ethyl vinyl ether

(2R,3S)-4-(4-methoxybenzyloxy)-3-methylbutane-1,2-diol

2-(6-methoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-propan-1-ol