{(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

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}methanol
• CAS No.: 498554-31-7
• Molecular Formula: C₃₂H₃₄Br₂O₆
• Molecular Weight: 674.426
• Mol file: 498554-31-7.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}methanol

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}methanol

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}methanol

There total 20 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}methanol 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:

(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-10-(tert-butyldimethylsilyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-ene (498554-30-6) → {(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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 15h;

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}methanol (498554-31-7)

Guidance literature:

Multi-step reaction with 18 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

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}methanol (498554-31-7)

Guidance literature:

Multi-step reaction with 17 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

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:

(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-10-(tert-butyldimethylsilyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-ene

(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

(1S,2S,3R,5R,8R,10S,12Z)-2-(tert-butyldimethylsilyloxy)-5-phenyl-4,6,9,15-tetraoxatricyclo[8.5.0.0^3,8]pentadec-12-en-14-one

Downstream raw materials:

{(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