3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol

Base Information

• Chemical Name: 3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol
• CAS No.: 147806-83-5
• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.537
• Mol file: 147806-83-5.mol

Synonyms:3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol

Chemical Property of 3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol

There total 16 articles about 3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol 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: 97.0%

3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-7-O-(tert-butyldimethylsilyl)-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol (143293-30-5) → 3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol (147806-83-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1021/ja00046a063

Reference yield:

((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol (132375-56-5) → 3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol (147806-83-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

2: 98 percent / TFA / toluene / 0.25 h / 0 °C

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

4: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

6: benzene / 2 h / 80 °C

7: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

8: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

9: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

10: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

11: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;

Reference yield:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-81-2) → 3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol (147806-83-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 80 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

2: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

3: 98 percent / TFA / toluene / 0.25 h / 0 °C

4: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

5: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

7: benzene / 2 h / 80 °C

8: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

9: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

10: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

11: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

12: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;

upstream raw materials:

3,4:6,10-dianhydro-8,11-O-dibenzyl-3-C-methyl-7-O-(tert-butyldimethylsilyl)-1,2,5,9-tetradeoxy-D-threo-L-altro-undec-1-enitol

benzyl bromide

((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

Downstream raw materials:

Hemibrevetoxin-B

(2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-one

(2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione

5,9:8,12-dianhydro-10,13-O-dibenzyl-5-C-methyl-2,3,4,7,11-pentadeoxy-D-threo-L-allo-trideconic acid