(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

Base Information

Chemical Name:(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate
CAS No.:887768-95-8
Molecular Formula:C₅₀H₇₀O₆Si₂
Molecular Weight:823.273
Hs Code.:

Synonyms:(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

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Chemical Property of (E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

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Technology Process of (E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

There total 14 articles about (E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate 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%

: 864712-67-4
(2R,3R,4R)-2,3-bis(benzyloxy)-10-t-butyldiphenylsiloxy-4-triethylsiloxy-4-methyldecanal

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 887768-95-8
(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

Guidance literature:: In benzene; at 100 ℃; for 13h;
DOI:10.1246/bcsj.79.468

Reference yield:

: 887769-09-7
((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-acetaldehyde

: 887768-95-8
(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1: 2.37 g / n-BuLi / tetrahydrofuran; hexane / 13 h / 20 °C

2: 2.38 g / H₂ / Pd-C / ethanol / 4 h

3: Et₂O*BF₃ / acetic anhydride / 0.5 h / -25 °C

4: K₂CO₃ / methanol / 3.5 h / 20 °C

5: 2.61 g / NaBH₄ / methanol / 2 h / 20 °C

6: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8: 100 percent / benzene / 13 h / 100 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetic anhydride; benzene; 1: Wittig reaction / 7: Swern oxidation / 8: Wittig reaction;
DOI:10.1246/bcsj.79.468

Reference yield:

: 864712-68-5
3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

: 887768-95-8
(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / 9-BBN / tetrahydrofuran / 16 h / 20 °C

2: 1.40 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 2.37 g / n-BuLi / tetrahydrofuran; hexane / 13 h / 20 °C

4: 2.38 g / H₂ / Pd-C / ethanol / 4 h

5: Et₂O*BF₃ / acetic anhydride / 0.5 h / -25 °C

6: K₂CO₃ / methanol / 3.5 h / 20 °C

7: 2.61 g / NaBH₄ / methanol / 2 h / 20 °C

8: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

10: 100 percent / benzene / 13 h / 100 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetic anhydride; benzene; 3: Wittig reaction / 9: Swern oxidation / 10: Wittig reaction;
DOI:10.1246/bcsj.79.468