(-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane

Base Information

• Chemical Name: (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane
• CAS No.: 165960-92-9
• Molecular Formula: C₂₇H₃₀N₂O₁₄S
• Molecular Weight: 638.606
• Mol file: 165960-92-9.mol

Synonyms:(-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane

Chemical Property of (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane

There total 4 articles about (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane 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: 57.0%

methanesulfonyl chloride (124-63-0) + (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-1,2,11,12-tetrahydroxydodecane (204637-90-1) → (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane (165960-92-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(97)10439-2

Reference yield:

4-nitro-benzoyl chloride (122-04-3) → (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane (165960-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / toluene; CH₂Cl₂ / 1 h / 0 °C

2: 92 percent / BF₃*Et₂O, H₂O / methanol; CH₂Cl₂ / 5 h / Ambient temperature

3: 37 percent / Et₃N / tetrahydrofuran / 0 °C

With boron trifluoride diethyl etherate; water; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo00119a019

Reference yield:

[(2S,3S)-3-(2-{(4R,5R)-5-[2-((2S,3S)-3-Hydroxymethyl-oxiranyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-oxiranyl]-methanol → (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane (165960-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / toluene; CH₂Cl₂ / 1 h / 0 °C

2: 92 percent / BF₃*Et₂O, H₂O / methanol; CH₂Cl₂ / 5 h / Ambient temperature

3: 37 percent / Et₃N / tetrahydrofuran / 0 °C

With boron trifluoride diethyl etherate; water; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo00119a019

upstream raw materials:

methanesulfonyl chloride

(-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-1,2,11,12-tetrahydroxydodecane

4-nitro-benzoyl chloride

(-)-(2S,3S,6R,7R,10S,11S)-2,3:10,11-Diepoxy-6,7-O-isopropylidene-1,12-O-bis(4-nitrobenzoyl)-1,6,7,12-tetrahydroxydodecane

Downstream raw materials:

C₂₉H₃₄N₂O₁₅S

Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-ethyl ester

Toluene-4-sulfonic acid (S)-2-methoxymethoxy-2-[(2R,5R,2'R,5'R)-5'-((R)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-ethyl ester

(+)-(2S,3R,6R,7R,10R,11R)-1-O-(tert-Butyldiphenylsilyl)-2-O-(methoxymethyl)-3,6:7,10-diepoxy-1,2,11-trihydroxyhenicosane