(2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane

Base Information

Chemical Name:(2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane
CAS No.:195377-41-4
Molecular Formula:C₅₅H₆₆O₇Si
Molecular Weight:867.21
Hs Code.:

Synonyms:(2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane

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Chemical Property of (2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane

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Technology Process of (2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane

There total 11 articles about (2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane 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:

: 78646-25-0
4-dimethylamino-1-N-(triphenylmethyl)pyridinium chloride

: 195377-41-4
(2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / CH₂Cl₂ / 7 h / Heating

2: 97 percent / sodium hydride / dimethylformamide / 1 h / 0 - 20 °C

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Methylation;
DOI:10.1021/ja970251g

Reference yield:

: 139190-51-5
Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

: 195377-41-4
(2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane

Guidance literature:: Multi-step reaction with 11 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

With dmap; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; 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;
DOI:10.1021/ja970251g

Reference yield:

: 139190-55-9
(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

: 195377-41-4
(2R,3S,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-methoxy-4-methoxymethoxy-3,5-dimethyl-1-trityloxyheptane

Guidance literature:: Multi-step reaction with 10 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

10.1: 97 percent / sodium hydride / dimethylformamide / 1 h / 0 - 20 °C

With dmap; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; 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: 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 / 10.1: Methylation;
DOI:10.1021/ja970251g