(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol

Base Information

• Chemical Name: (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol
• CAS No.: 195377-53-8
• Molecular Formula: C₅₄H₆₄O₇Si
• Molecular Weight: 853.183
• Mol file: 195377-53-8.mol

Synonyms:(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol

Chemical Property of (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol

There total 10 articles about (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol 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: 60.0%

4-dimethylamino-1-N-(triphenylmethyl)pyridinium chloride (78646-25-0) + (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol (195377-52-7) → (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol (195377-53-8)

Guidance literature:

In dichloromethane; for 7h; Heating;

DOI:10.1021/ja970251g

Reference yield:

Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5) → (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol (195377-53-8)

Guidance literature:

Multi-step reaction with 10 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

With dmap; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 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;

DOI:10.1021/ja970251g

Reference yield:

(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester (139190-55-9) → (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-1-trityloxy-heptan-2-ol (195377-53-8)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: 91 percent / Davis oxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

2.1: 92 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 48 h / 0 - 20 °C

3.1: 97 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C

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

5.1: 8.5 g / CH₂Cl₂ / 14 h / 20 °C

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

6.2: 85 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C

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

7.2: 80 percent / Davis oxaziridine reagent / tetrahydrofuran; toluene / 3 h / -78 °C

8.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O / 72 h / 20 °C

9.1: 60 percent / CH₂Cl₂ / 7 h / Heating

With dmap; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; 1.1: Metallation / 1.2: Oxidation / 2.1: Etherification / 3.1: Reduction / 4.1: Swern oxidation / 5.1: Wittig reaction / 6.1: complexation / 6.2: Addition / 7.1: Metallation / 7.2: Oxidation / 8.1: Reduction / 9.1: Etherification;

DOI:10.1021/ja970251g

upstream raw materials:

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

(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol

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

(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

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

(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

(2R,3S,4S,5S,6S,7S,8R)-2,4-Bis-benzyloxymethoxy-8-methoxy-6-methoxymethoxy-3,5,7-trimethyl-9-trityloxy-nonanoic acid methyl ester