(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

Base Information

• Chemical Name: (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
• CAS No.: 195377-48-1
• Molecular Formula: C₅₄H₆₈O₁₀
• Molecular Weight: 877.128
• Mol file: 195377-48-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 23 articles about (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 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: 86.0%

methyllithium-lithium bromide + (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) → (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 (195377-48-1)

Guidance literature:

methyllithium-lithium bromide; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at -15 - 0 ℃; for 0.5h;

(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; With chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 3.5h;

DOI:10.1021/ja970251g

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (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 (195377-48-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 77 percent / diisopropylethylamine / CH₂Cl₂ / 60 h / 0 - 20 °C

2.1: 83 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C

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

4.1: 87 mg / CH₂Cl₂ / 14 h / 20 °C

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

5.2: 86 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C

With copper(l) iodide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Etherification / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Wittig reaction / 5.1: complexation / 5.2: Addition;

DOI:10.1021/ja970251g

Reference yield:

4-dimethylamino-1-N-(triphenylmethyl)pyridinium chloride (78646-25-0) → (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 (195377-48-1)

Guidance literature:

Multi-step reaction with 12 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

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

12.2: 86 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °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 / 12.1: complexation / 12.2: Addition;

DOI:10.1021/ja970251g

upstream raw materials:

(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

Benzyloxymethyl chloride

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

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