(4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester

Base Information

• Chemical Name: (4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester
• CAS No.: 195377-47-0
• Molecular Formula: C₅₃H₆₄O₁₀
• Molecular Weight: 861.085
• Mol file: 195377-47-0.mol

Synonyms:(4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester

Chemical Property of (4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester

There total 22 articles about (4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester 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:

Benzyloxymethyl chloride (3587-60-8) → (4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester (195377-47-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / diisopropylethylamine / CH₂Cl₂ / 60 h / 0 - 20 °C

2: 83 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C

3: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.83 h / -55 - -30 °C

4: 87 mg / CH₂Cl₂ / 14 h / 20 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 1: Etherification / 2: Reduction / 3: Swern oxidation / 4: Wittig reaction;

DOI:10.1021/ja970251g

Reference yield:

4-dimethylamino-1-N-(triphenylmethyl)pyridinium chloride (78646-25-0) → (4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester (195377-47-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 60 percent / CH₂Cl₂ / 7 h / Heating

2.1: 97 percent / sodium hydride / dimethylformamide / 1 h / 0 - 20 °C

3.1: 96 percent / TBAF / tetrahydrofuran / 4.5 h / 20 °C

4.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.83 h / -55 - -30 °C

5.1: 34 mg / CH₂Cl₂ / 14 h / 20 °C

6.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C

6.2: 83 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C

7.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.2: 76 percent / Davis oxaziridine reagent / tetrahydrofuran; toluene / 3 h / -78 °C

8.1: 77 percent / diisopropylethylamine / CH₂Cl₂ / 60 h / 0 - 20 °C

9.1: 83 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C

10.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.83 h / -55 - -30 °C

11.1: 87 mg / CH₂Cl₂ / 14 h / 20 °C

With copper(l) iodide; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Methylation / 3.1: desilylation / 4.1: Swern oxidation / 5.1: Wittig reaction / 6.1: complexation / 6.2: Addition / 7.1: Metallation / 7.2: Oxidation / 8.1: Etherification / 9.1: Reduction / 10.1: Swern oxidation / 11.1: Wittig reaction;

DOI:10.1021/ja970251g

Reference yield:

Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5) → (4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-5,7,9-trimethyl-11-trityloxy-undec-2-enoic acid methyl ester (195377-47-0)

Guidance literature:

Multi-step reaction with 20 steps

1.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C

1.2: 92 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: 91 percent / Davis oxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

3.1: 92 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 48 h / 0 - 20 °C

4.1: 97 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C

5.1: oxalyl chloride; DMSO; triethylamin / CH₂Cl₂ / 0.83 h / -55 - -30 °C

6.1: 8.5 g / CH₂Cl₂ / 14 h / 20 °C

7.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C

7.2: 85 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C

8.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

8.2: 80 percent / Davis oxaziridine reagent / tetrahydrofuran; toluene / 3 h / -78 °C

9.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O / 72 h / 20 °C

10.1: 60 percent / CH₂Cl₂ / 7 h / Heating

11.1: 97 percent / sodium hydride / dimethylformamide / 1 h / 0 - 20 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 4.5 h / 20 °C

13.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.83 h / -55 - -30 °C

14.1: 34 mg / CH₂Cl₂ / 14 h / 20 °C

15.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C

15.2: 83 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C

16.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

16.2: 76 percent / Davis oxaziridine reagent / tetrahydrofuran; toluene / 3 h / -78 °C

17.1: 77 percent / diisopropylethylamine / CH₂Cl₂ / 60 h / 0 - 20 °C

18.1: 83 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C

19.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.83 h / -55 - -30 °C

20.1: 87 mg / CH₂Cl₂ / 14 h / 20 °C

With dmap; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: complexation / 1.2: Addition / 2.1: Metallation / 2.2: Oxidation / 3.1: Etherification / 4.1: Reduction / 5.1: Swern oxidation / 6.1: Wittig reaction / 7.1: complexation / 7.2: Addition / 8.1: Metallation / 8.2: Oxidation / 9.1: Reduction / 10.1: Etherification / 11.1: Methylation / 12.1: desilylation / 13.1: Swern oxidation / 14.1: Wittig reaction / 15.1: complexation / 15.2: Addition / 16.1: Metallation / 16.2: Oxidation / 17.1: Etherification / 18.1: Reduction / 19.1: Swern oxidation / 2;

DOI:10.1021/ja970251g

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

Benzyloxymethyl chloride

4-dimethylamino-1-N-(triphenylmethyl)pyridinium chloride

Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

Downstream raw materials:

(2S,3S,4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-2-hydroxy-10-methoxy-8-methoxymethoxy-3,5,7,9-tetramethyl-11-trityloxyundecanoic acid methyl ester

(3S,4S,5R,6R,7R,8S,9S,10R)-4,6-bis-[(benzyloxy)methoxy]-10-methoxy-8-methoxymethoxy-3,5,7,9-tetramethyl-11-trityloxyundecanoic acid methyl ester