(2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin

Base Information

• Chemical Name: (2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin
• CAS No.: 863222-45-1
• Molecular Formula: C₃₃H₄₂O₆
• Molecular Weight: 534.693
• Mol file: 863222-45-1.mol

Synonyms:(2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin

Chemical Property of (2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin

There total 1 articles about (2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin 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: 50.0%

(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}hex-5-en-1,3-diol (863222-68-8) + 2,2-dimethoxy-propane (77-76-9) → (2R,3S,4Z,6R,7S,4'S,5'S)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin + (2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin (863222-45-1)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 24 ℃; for 3h;

DOI:10.1016/j.tet.2005.05.073

Reference yield: 97.0%

(2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin (863222-45-1) → (1S,3R,8S,10Z,13R,15S,16R,17Z)-16-benzyloxy-15-benzyloxymethyl-6,6-dimethyl-2,5,7,14-tetraoxatricyclo[11.5.0.03,8]octadeca-10,17-diene

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 23 ℃; for 4h;

DOI:10.1016/j.tet.2005.05.073

Reference yield:

(2R,3S,4Z,6R,7S,4'S,5'R)-2-allyl-3-{(4'-allyl-2',2'-dimethyl-1',3'-dioxan-5'-yl)oxy}-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin (863222-45-1) → (1S,3R,4S,6Z,9R,11S,12R,13Z)-12-benzyloxy-11-benzyloxymethyl-3-hydroxymethyl-2,10-dioxabicyclo[7.5.0]tetradeca-6,13-dien-4-ol

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 4 h / 23 °C

2: 88 percent / TFA; H₂O / tetrahydrofuran / 3 h / 23 °C

With Grubbs catalyst first generation; water; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.05.073

upstream raw materials:

(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}hex-5-en-1,3-diol

2,2-dimethoxy-propane