tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Base Information

• Chemical Name: tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate
• CAS No.: 925453-69-6
• Molecular Formula: C₄₉H₇₁BrO₁₄Si
• Molecular Weight: 992.084
• Mol file: 925453-69-6.mol

Synonyms:tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Chemical Property of tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

There total 5 articles about tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 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: 96.0%

bromomethyldimethylsilyl chloride (16532-02-8) + tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-(4-hydroxy-5-methyl-6-phenyl-2-hexenyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate → tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate (925453-69-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/chem.200601212

Reference yield:

(2S,3R)-1,2-epoxy-3-methyl-4-phenylbutane (219607-74-6) → tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate (925453-69-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -20 °C

1.2: 87 percent / tetrahydrofuran; hexane / -20 - 20 °C

2.1: 96 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 1 h / 20 °C

3.1: 62 percent / Hoveyda's catalyst / benzene / 70 °C

4.1: 84 percent / diisobutylaluminum hydride / toluene; CH₂Cl₂ / 0.5 h / -78 °C

5.1: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; dmap; n-butyllithium; diisobutylaluminium hydride; triethylamine; dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II); In tetrahydrofuran; hexane; dichloromethane; toluene; benzene;

DOI:10.1002/chem.200601212

Reference yield:

(3R,4R)-4-methyl-5-phenyl-1-penten-3-ol (925453-63-0) → tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-1-[4-[(bromomethyl)dimethylsilyl]oxy-5-methyl-6-phenyl-2-hexenyl]-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate (925453-69-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 1 h / 20 °C

2: 62 percent / Hoveyda's catalyst / benzene / 70 °C

3: 84 percent / diisobutylaluminum hydride / toluene; CH₂Cl₂ / 0.5 h / -78 °C

4: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; dmap; diisobutylaluminium hydride; triethylamine; dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II); In dichloromethane; toluene; benzene;

DOI:10.1002/chem.200601212

upstream raw materials:

bromomethyldimethylsilyl chloride

(2S,3R)-1,2-epoxy-3-methyl-4-phenylbutane

(3R,4R)-4-methyl-5-phenyl-1-penten-3-ol

(3R,4R)-4-methyl-5-phenyl-1-penten-3-yl acetate

Downstream raw materials:

6-benzyloxy-7-tert-butoxycarbonyloxy-1-{2-[2,2-dimethyl-5-(1-methyl-2-phenyl-ethyl)-[1,2]oxasilolan-4-yl]-ethyl}-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

tri-tert-butyl [1S,1(3R,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-3-(hydroxymethyl)-5-methyl-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-6-acetoxy-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate