C₈₂H₁₄₉NO₁₂S₂Si₃

Base Information

• Chemical Name: C₈₂H₁₄₉NO₁₂S₂Si₃
• CAS No.: 128685-08-5
• Molecular Formula: C₈₂H₁₄₉NO₁₂S₂Si₃
• Molecular Weight: 1489.47
• Mol file: 128685-08-5.mol

Synonyms:

Chemical Property of C₈₂H₁₄₉NO₁₂S₂Si₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₈₂H₁₄₉NO₁₂S₂Si₃

There total 90 articles about C₈₂H₁₄₉NO₁₂S₂Si₃ 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:

(2R,8R)-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone (128685-04-1) → C82H149NO12S2Si3 (128685-08-5,128777-59-3)

Guidance literature:

Multi-step reaction with 12 steps

1: trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 3 h

2: 1.0 N aq. NaOH / tetrahydrofuran; methanol / 0.17 h

3: NaH / dimethylformamide / 0.67 h / 0 - 20 °C

4: 98 percent / H₂ / 5percent Pd(OH)2/C / ethyl acetate / 13 h / 760 Torr

5: 293 mg / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h

6: L-Selectride / tetrahydrofuran / 1.5 h / -78 °C

7: BF₃*OEt₂ / CH₂Cl₂ / 1.) from -78 to 0 deg C, 70 min, 2.) RT, 13 h

8: 93 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

9: 69 percent / I₂, PPh₃, pyridine / benzene / 1.) 0 deg C, 1 h, 2.) RT, 6 h

10: 100 percent / Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

11: 1.) n-BuLi / 1.) THF, hexanes, 0 deg C, 40 min, 2.) a) -78 deg C, 25 min, b) 0 deg C, 3 h

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; iodine; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00170a024

Reference yield:

(2R,8R)-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone (128685-04-1) → C82H149NO12S2Si3 (128685-08-5,128777-59-3)

Guidance literature:

Multi-step reaction with 12 steps

1: trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 3 h

2: 1.0 N aq. NaOH / tetrahydrofuran; methanol / 0.17 h

3: NaH / dimethylformamide / 0.67 h / 0 - 20 °C

4: 98 percent / H₂ / 5percent Pd(OH)2/C / ethyl acetate / 13 h / 760 Torr

5: 293 mg / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h

6: L-Selectride / tetrahydrofuran / 1.5 h / -78 °C

7: BF₃*OEt₂ / CH₂Cl₂ / 1.) from -78 to 0 deg C, 70 min, 2.) RT, 13 h

8: 93 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

9: 69 percent / I₂, PPh₃, pyridine / benzene / 1.) 0 deg C, 1 h, 2.) RT, 6 h

10: 100 percent / Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

11: 1.) n-BuLi / 1.) THF, hexanes, 0 deg C, 40 min, 2.) a) -78 deg C, 25 min, b) 0 deg C, 3 h

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; iodine; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00170a024

Reference yield:

(2R,8R)-5-O-(tert-butyldimethylsilyl)-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone (128685-03-0) → C82H149NO12S2Si3 (128685-08-5,128777-59-3)

Guidance literature:

Multi-step reaction with 13 steps

1: HF / acetonitrile / 60 h / Ambient temperature

2: trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 3 h

3: 1.0 N aq. NaOH / tetrahydrofuran; methanol / 0.17 h

4: NaH / dimethylformamide / 0.67 h / 0 - 20 °C

5: 98 percent / H₂ / 5percent Pd(OH)2/C / ethyl acetate / 13 h / 760 Torr

6: 293 mg / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h

7: L-Selectride / tetrahydrofuran / 1.5 h / -78 °C

8: BF₃*OEt₂ / CH₂Cl₂ / 1.) from -78 to 0 deg C, 70 min, 2.) RT, 13 h

9: 93 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

10: 69 percent / I₂, PPh₃, pyridine / benzene / 1.) 0 deg C, 1 h, 2.) RT, 6 h

11: 100 percent / Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

12: 1.) n-BuLi / 1.) THF, hexanes, 0 deg C, 40 min, 2.) a) -78 deg C, 25 min, b) 0 deg C, 3 h

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja00170a024

upstream raw materials:

(2RS,4R,6S,7R,8S,10R)-2--7-<(tert-butyldimethylsilyl)oxy>-6,8-dimethoxy-10-(1,3-dithian-2-yl)-4-methylundecane

<1(1R,3R,4R),1E,3(2S),3S,4S,5S,7S,8S>-3--7-<(4-methoxybenzyl)oxy>-1-<3-methoxy-4-<(triisopropylsilyl)oxy>cyclohex-1-yl>-2,4-dimethyl-8-(2-propen-1-yl)-5-<(triisopropylsilyl)oxy>-1-nonen-9-al

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

triisopropylsilyl trifluoromethanesulfonate