{(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate

Base Information

• Chemical Name: {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate
• CAS No.: 498554-32-8
• Molecular Formula: C₃₃H₃₃Br₂F₃O₈S
• Molecular Weight: 806.489
• Mol file: 498554-32-8.mol

Synonyms:{(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate

Chemical Property of {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate

There total 21 articles about {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate 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: 95.0%

trifluoromethylsulfonic anhydride (358-23-6) + {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methanol (498554-31-7) → {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate (498554-32-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)01329-7

Reference yield:

4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucopyranose → {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate (498554-32-8)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: titanocene dichloride / toluene / 72 h / 23 °C

2.2: 742.4 mg / toluene; tetrahydrofuran / 0 - 23 °C

3.1: 9-BBN / tetrahydrofuran / 2 h / 23 °C

3.2: 85 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 11 h / 23 °C

4.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

5.1: BuLi / tetrahydrofuran / 1 h / -78 °C

5.2: CuCN / tetrahydrofuran / -78 - 0 °C

5.3: 93 percent / tetrahydrofuran / -78 - 0 °C

6.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C

7.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 99 percent / i-Pr₂NEt / CH₂Cl₂ / 3.5 h / 25 °C

9.1: 85 percent / (1,3-diMes-4,5-dihydroimidazol-2-yl)Ru(PCy₃)Cl₂(benzylidene) / 1,2-dichloro-ethane / 12 h / 120 °C

10.1: titanocene dichloride / toluene / 72 h / 23 °C

10.2: 82 percent / toluene; tetrahydrofuran / 0.5 h / -40 °C

11.1: 9-BBN / tetrahydrofuran / 0.83 h / 25 °C

11.2: 59 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 12 h / 24 °C

12.1: TBAI; NaH / tetrahydrofuran / 14 h / 25 °C

13.1: 38.8 mg / TBAF / tetrahydrofuran / 16 h / 25 °C

14.1: 99 percent / TBAI; NaH / tetrahydrofuran / 5 h / 25 °C

15.1: 99 percent / aq. HCl / tetrahydrofuran / 12 h / 25 °C

16.1: 100 percent / DMAP; Et₃N / CH₂Cl₂ / 9.5 h / 25 °C

17.1: TBAI; NaH / tetrahydrofuran / 12 h / 24 °C

18.1: 39.0 mg / TBAF / tetrahydrofuran / 15 h / 25 °C

19.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; hydrogenchloride; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; titanocene dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; 1.1: Swern oxidation / 2.2: Tebbe olefination / 10.2: Tebbe olefination;

DOI:10.1016/S0040-4020(02)01329-7

Reference yield:

4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone (498554-12-4) → {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate (498554-32-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: titanocene dichloride / toluene / 72 h / 23 °C

1.2: 742.4 mg / toluene; tetrahydrofuran / 0 - 23 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 23 °C

2.2: 85 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 11 h / 23 °C

3.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

4.1: BuLi / tetrahydrofuran / 1 h / -78 °C

4.2: CuCN / tetrahydrofuran / -78 - 0 °C

4.3: 93 percent / tetrahydrofuran / -78 - 0 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C

6.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 99 percent / i-Pr₂NEt / CH₂Cl₂ / 3.5 h / 25 °C

8.1: 85 percent / (1,3-diMes-4,5-dihydroimidazol-2-yl)Ru(PCy₃)Cl₂(benzylidene) / 1,2-dichloro-ethane / 12 h / 120 °C

9.1: titanocene dichloride / toluene / 72 h / 23 °C

9.2: 82 percent / toluene; tetrahydrofuran / 0.5 h / -40 °C

10.1: 9-BBN / tetrahydrofuran / 0.83 h / 25 °C

10.2: 59 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 12 h / 24 °C

11.1: TBAI; NaH / tetrahydrofuran / 14 h / 25 °C

12.1: 38.8 mg / TBAF / tetrahydrofuran / 16 h / 25 °C

13.1: 99 percent / TBAI; NaH / tetrahydrofuran / 5 h / 25 °C

14.1: 99 percent / aq. HCl / tetrahydrofuran / 12 h / 25 °C

15.1: 100 percent / DMAP; Et₃N / CH₂Cl₂ / 9.5 h / 25 °C

16.1: TBAI; NaH / tetrahydrofuran / 12 h / 24 °C

17.1: 39.0 mg / TBAF / tetrahydrofuran / 15 h / 25 °C

18.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; hydrogenchloride; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; titanocene dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; 1.2: Tebbe olefination / 9.2: Tebbe olefination;

DOI:10.1016/S0040-4020(02)01329-7

upstream raw materials:

trifluoromethylsulfonic anhydride

{(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methanol

(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol