(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal
• CAS No.: 887769-16-6
• Molecular Formula: C₅₈H₈₀O₇Si₂
• Molecular Weight: 945.44
• Mol file: 887769-16-6.mol

Synonyms:

Chemical Property of (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal

There total 26 articles about (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal 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,3R,4R)-2,3-bis(benzyloxy)-10-t-butyldiphenylsiloxy-4-triethylsiloxy-4-methyldecanal (864712-67-4) → (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal (887769-16-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran

1.2: DIBAL-H / CH₂Cl₂; tetrahydrofuran

2.1: 20 percent / Ti(O-iPr)4; D-(-)-DET; t-butylhydroperoxide / CH₂Cl₂

3.1: 87 percent / CuCN / diethyl ether / 8 h / 0 °C

4.1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / 20 °C

5.1: 64 percent / DIBAL-H / toluene / 8 h / 0 °C

6.1: 98.1 mg / Dess Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 6.1: Dess Martin oxidation;

DOI:10.1246/bcsj.79.468

Reference yield:

(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-2,6-dimethyldodeca-1-ol (864712-77-6) → (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal (887769-16-6)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane;

DOI:10.1016/j.tetlet.2005.06.079

Reference yield:

(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate (887768-95-8) → (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-triethylsilanyloxy-dodecanal (887769-16-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 40 h / 0 - 20 °C

2: 100 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

3: 81 percent / benzene / 1.5 h / 20 °C

4: 515 mg / 4-(dimethylamino)pyridine / pyridine / 12 h / 20 °C

5: 424 mg / NaOMe / methanol; tetrahydrofuran / 4 h / 0 °C

6: 87 percent / CuCN / diethyl ether / 8 h / 0 °C

7: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / 20 °C

8: 64 percent / DIBAL-H / toluene / 8 h / 0 °C

9: 98.1 mg / Dess Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

With dmap; lithium borohydride; sodium methylate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; osmium(VIII) oxide; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 9: Dess Martin oxidation;

DOI:10.1246/bcsj.79.468

upstream raw materials:

(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-2,6-dimethyldodeca-1-ol

3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-acetaldehyde

2-((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-ethanol

Downstream raw materials:

(E,4S,5R,6S,7R,8R)-methyl 6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-enoate

(E)-3-{(2R,3R)-3-[(1R,2R,3S,4R,5R)-3,4-Bis-benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1,5-dimethyl-5-triethylsilanyloxy-undecyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

(2S,3R)-3-[(1R,2R,3S,4R,5R)-3,4-Bis-benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-1,5-dimethyl-5-triethylsilanyloxy-undecyl]-2-methyl-oxirane-2-carbaldehyde

{(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol