(12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

Base Information

• Chemical Name: (12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane
• CAS No.: 443303-95-5
• Molecular Formula: C₃₇H₆₂O₇
• Molecular Weight: 618.895
• Mol file: 443303-95-5.mol

Synonyms:(12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

Chemical Property of (12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

There total 18 articles about (12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane 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: 80.0%

(12R,15S,16R/S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane (313963-51-8) → (12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane (443303-95-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 1.5h;

DOI:10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO;2-8

Reference yield:

benzyl bromide (100-39-0) → (12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane (443303-95-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 80 percent / tetrahydrofuran / -72 - 20 °C

2.1: TBAF / tetrahydrofuran / 2 h / 28 °C

3.1: H₂ / Raney nickel / ethanol / 0.5 h / 20 °C

4.1: DMSO; (COCl)2; NEt₃ / CH₂Cl₂ / -78 - 0 °C

5.1: nBuLi / tetrahydrofuran / 0.5 h / -78 - 0 °C

5.2: tetrahydrofuran / -78 °C

6.1: 91 percent / H₂ / Raney nickel / ethanol / 0.5 h / 20 °C

7.1: tetrapropylammonium perruthenate; NMO; NEt₃ / CH₂Cl₂ / 0.75 h / 0 °C

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; nickel; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Metallation / 1.2: Etherification / 2.1: Silyl ether cleavage / 3.1: Catalytic hydrogenation / 4.1: Swern oxidation / 5.1: Elimination / 5.2: Addition / 6.1: Catalytic hydrogenation / 7.1: Oxidation;

DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

Reference yield:

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol (201472-26-6) → (12R,15S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(propan-16-onyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane (443303-95-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / Amberlist 15 / benzene / 0.25 h / Heating

2.1: nBuLi / tetrahydrofuran / 0.5 h / -78 °C

2.2: Bu₃SnCl / tetrahydrofuran / 0.5 h / -78 - 20 °C

2.3: BF₃*OEt₂ / CH₂Cl₂ / 0.08 h / -10 °C

3.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: 80 percent / tetrahydrofuran / -72 - 20 °C

4.1: TBAF / tetrahydrofuran / 2 h / 28 °C

5.1: H₂ / Raney nickel / ethanol / 0.5 h / 20 °C

6.1: DMSO; (COCl)2; NEt₃ / CH₂Cl₂ / -78 - 0 °C

7.1: nBuLi / tetrahydrofuran / 0.5 h / -78 - 0 °C

7.2: tetrahydrofuran / -78 °C

8.1: 91 percent / H₂ / Raney nickel / ethanol / 0.5 h / 20 °C

9.1: tetrapropylammonium perruthenate; NMO; NEt₃ / CH₂Cl₂ / 0.75 h / 0 °C

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; Amberlist 15; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; nickel; In tetrahydrofuran; ethanol; dichloromethane; benzene; 1.1: Etherification / 2.1: Metallation / 2.2: Stannylation / 2.3: Rearrangement / 3.1: Metallation / 3.2: Etherification / 4.1: Silyl ether cleavage / 5.1: Catalytic hydrogenation / 6.1: Swern oxidation / 7.1: Elimination / 7.2: Addition / 8.1: Catalytic hydrogenation / 9.1: Oxidation;

DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

upstream raw materials:

(12R,15S,16R/S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

benzyl bromide

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

[(2R,3S,5R,6R)-3-(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]methanol

Downstream raw materials:

(12R,15S,16S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-hydroxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane

(12R,15S,16S,19R,20S,34R,35R)-34,35-dimethoxy-34,35-dimethyl-19-(12-(9-benzyloxypropyl)-15-(16-tert-butyldimethylsilyloxypropyl)tetrahydrofuran)-20-dodecanyl-[33,36]-dioxane