3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide

Base Information

• Chemical Name: 3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide
• CAS No.: 122624-84-4
• Molecular Formula: C₅₁H₇₄O₆PSi₂*I
• Molecular Weight: 997.194

Synonyms:3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide

Chemical Property of 3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide

There total 27 articles about 3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide 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%

(2S,3R,4aS,6R,7S,8aR)-7-<(Benzyloxy)methoxy>-6-<3-(tert-butyldimethylsiloxy)propyl>-2-(2-iodoethyl)-2,4a,6-trimethyl-3-(trimethylsiloxy)perhydropyrano<3,2-b>pyran (122625-11-0) + triphenylphosphine (603-35-0) → 3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide (122624-84-4)

Guidance literature:

In acetonitrile; at 90 ℃; for 24h;

DOI:10.1021/ja00199a030

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide (122624-84-4)

Guidance literature:

Multi-step reaction with 26 steps

1: 84 percent / NEt(i-Pr)2 / 1,2-dichloro-ethane / 18 h / 75 °C

2: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

3: 82 percent / benzene / 18 h / 70 °C

4: 100 percent / 1,2-dichloro-ethane / 6 h / 60 °C

5: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

6: 1.) 4A molecular sieves, D-(-)-diethyl tartrate, Ti(O-iPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) -20 deg C, 16 h

7: SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

8: 79 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

9: 96 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

10: 83 percent / (1S)-(+)-10-camphorsulfonic acid / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) 1.5 h

11: 100 percent / CH₂Cl₂ / 2 h / 25 °C

12: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

13: 1.) BH₃e*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 45 min; r.t., 20 min, 2.) 0 deg C, 20 min

14: 75 percent / benzene / 3 h / 25 °C

15: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

16: 1.) 4A molecular sieves, D-(-)-diethyl tartrate, Ti(O-iPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) -20 deg C, 16 h

17: 90 percent / SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 4 h / 0 °C

18: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min

19: 97 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 25 °C

20: 85 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 2 h

21: 100 percent / CH₂Cl₂ / 2 h / 25 °C

22: 1.) BH₃*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 45 min; r.t., 20 min, 2.) 0 deg C, 20 min

23: 89 percent / I₂, Ph₃P, imidazole / benzene / 0.33 h / 10 °C

24: 1.) ozone, 2.) BF₃*SMe₂ / 1.) -78 deg C, CH₂Cl₂, 2.) THF, 30 min

25: 98 percent / imidazole / dimethylformamide / 1 h / 0 °C

26: 100 percent / acetonitrile / 24 h / 90 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; boron dimethyl-trifluoro sulphide; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; ozone; (+)-10-camphorsulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja00199a030

Reference yield:

(4S,5R)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one (122624-85-5) → 3,7:6,10-Dianhydro-9-O-<(benzyloxy)methyl>-13-O-(tert-butyldimethylsilyl)-1,2,5,8,11,12-hexadeoxy-3,6,10-tri-C-methyl-4-O-(trimethylsilyl)-1-(triphenylphosphonio)-D-erythro-D-allo-tridecitol iodide (122624-84-4)

Guidance literature:

Multi-step reaction with 26 steps

1: 84 percent / NEt(i-Pr)2 / 1,2-dichloro-ethane / 18 h / 75 °C

2: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

3: 82 percent / benzene / 18 h / 70 °C

4: 100 percent / 1,2-dichloro-ethane / 6 h / 60 °C

5: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

6: 1.) 4A molecular sieves, D-(-)-diethyl tartrate, Ti(O-iPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) -20 deg C, 16 h

7: SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

8: 79 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

9: 96 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

10: 83 percent / (1S)-(+)-10-camphorsulfonic acid / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) 1.5 h

11: 100 percent / CH₂Cl₂ / 2 h / 25 °C

12: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

13: 1.) BH₃e*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 45 min; r.t., 20 min, 2.) 0 deg C, 20 min

14: 75 percent / benzene / 3 h / 25 °C

15: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

16: 1.) 4A molecular sieves, D-(-)-diethyl tartrate, Ti(O-iPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) -20 deg C, 16 h

17: 90 percent / SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 4 h / 0 °C

18: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min

19: 97 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 25 °C

20: 85 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 2 h

21: 100 percent / CH₂Cl₂ / 2 h / 25 °C

22: 1.) BH₃*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 45 min; r.t., 20 min, 2.) 0 deg C, 20 min

23: 89 percent / I₂, Ph₃P, imidazole / benzene / 0.33 h / 10 °C

24: 1.) ozone, 2.) BF₃*SMe₂ / 1.) -78 deg C, CH₂Cl₂, 2.) THF, 30 min

25: 98 percent / imidazole / dimethylformamide / 1 h / 0 °C

26: 100 percent / acetonitrile / 24 h / 90 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; boron dimethyl-trifluoro sulphide; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; ozone; (+)-10-camphorsulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja00199a030

upstream raw materials:

(2S,3R,4aS,6R,7S,8aR)-7-<(Benzyloxy)methoxy>-6-<3-(tert-butyldimethylsiloxy)propyl>-2-(2-iodoethyl)-2,4a,6-trimethyl-3-(trimethylsiloxy)perhydropyrano<3,2-b>pyran

triphenylphosphine

Benzyloxymethyl chloride

(4S,5R)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one

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