((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide

Base Information

• Chemical Name: ((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide
• CAS No.: 79386-68-8
• Molecular Formula: Br*C₄₀H₅₄O₅P
• Molecular Weight: 725.744
• Mol file: 79386-68-8.mol

Synonyms:((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide

Chemical Property of ((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide

There total 19 articles about ((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide 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: 100.0%

(4S,5R,6S)-4-((E)-(S)-4-Bromo-1-methyl-but-2-enyl)-6-[(S)-1-((2R,3R,4S,6R)-4,6-dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxane (79386-67-7) + triphenylphosphine (603-35-0) → ((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide (79386-68-8)

Guidance literature:

In diethyl ether; at 30 ℃; for 48h;

DOI:10.1246/bcsj.54.1743

Reference yield:

(E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2S,3S,4R,5R,6R)-5-Bromo-4,6-dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-en-1-ol (79386-65-5) → ((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide (79386-68-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / Et₃N, LiBr, mesyl chloride / CH₂Cl₂ / 13 h / 0 - 20 °C

2: 100 percent / benzene / 120 h / 55 °C

3: 1.) BuLi / 1.) THF, hexane, -75 deg C, 15 min, 2.) THF, hexane, -75 deg C

4: 100 percent / 90percent TFA / H₂O / 0.25 h / 0 °C

5: 90 percent / DMAP / ethyl acetate / 24 h / 45 °C

6: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -75 deg C, 2.) CH₂Cl₂, -75 deg C to RT, 3 h

7: 84 percent / benzene / 3 h / Heating

8: 95 percent / tributylstannane, AIBN / benzene / 3 h / 60 °C

9: DIBAL / toluene; hexane / 0.17 h / -75 °C

10: 73 percent / dimethylformamide / 5 h / Ambient temperature

11: 80 percent / Et₃N, LiBr, mesyl chloride / CH₂Cl₂ / 13 h / 0 - 20 °C

12: 100 percent / diethyl ether / 48 h / 30 °C

With dmap; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; ozone; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; lithium bromide; In diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1246/bcsj.54.1743

Reference yield:

(E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2S,3S,4R,5R,6R)-5-Bromo-4,6-dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester (79386-63-3) → ((E)-(S)-4-{(4S,5R,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-enyl)-triphenyl-phosphonium; bromide (79386-68-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 96 percent / DIBAL / toluene; hexane / 0.5 h / -75 °C

2: 90 percent / Et₃N, LiBr, mesyl chloride / CH₂Cl₂ / 13 h / 0 - 20 °C

3: 100 percent / benzene / 120 h / 55 °C

4: 1.) BuLi / 1.) THF, hexane, -75 deg C, 15 min, 2.) THF, hexane, -75 deg C

5: 100 percent / 90percent TFA / H₂O / 0.25 h / 0 °C

6: 90 percent / DMAP / ethyl acetate / 24 h / 45 °C

7: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -75 deg C, 2.) CH₂Cl₂, -75 deg C to RT, 3 h

8: 84 percent / benzene / 3 h / Heating

9: 95 percent / tributylstannane, AIBN / benzene / 3 h / 60 °C

10: DIBAL / toluene; hexane / 0.17 h / -75 °C

11: 73 percent / dimethylformamide / 5 h / Ambient temperature

12: 80 percent / Et₃N, LiBr, mesyl chloride / CH₂Cl₂ / 13 h / 0 - 20 °C

13: 100 percent / diethyl ether / 48 h / 30 °C

With dmap; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; ozone; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; lithium bromide; In diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1246/bcsj.54.1743

upstream raw materials:

(4S,5R,6S)-4-((E)-(S)-4-Bromo-1-methyl-but-2-enyl)-6-[(S)-1-((2R,3R,4S,6R)-4,6-dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxane

triphenylphosphine

(R)-2-{(4R,5S,6S)-6-[(S)-1-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

methyl 2,4,6,8,10,11,12-heptadeoxy-7,9-O-isopropylidene-4,6,8,10-tetra-C-methyl-3-O-methyl-L-manno-β-D-galacto-(E)-11-tridecenopyranoside-(1,5)