benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate

Base Information

Chemical Name:benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate
CAS No.:616890-48-3
Molecular Formula:C₃₆H₄₉NO₅Si
Molecular Weight:603.874
Hs Code.:

Synonyms:benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate

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Chemical Property of benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate

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Technology Process of benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate

There total 6 articles about benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-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:

: 7396-44-3
benzyl diethylphosphonoacetate

: (2R,3R)-3-(dibenzylamino)-5-(tert-butyldimethylsilyloxy)-2-(methoxymethoxy)pentanal

: 616890-48-3
benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate

Guidance literature:: benzyl diethylphosphonoacetate; With sodium hydride; In toluene;

(2R,3R)-3-(dibenzylamino)-5-(tert-butyldimethylsilyloxy)-2-(methoxymethoxy)pentanal; In toluene; at 0 ℃; for 2h;
DOI:10.1021/jm0302086

Reference yield:

: (2R)-4-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)butanal

: 616890-48-3
benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4.87 g / tetrahydrofuran / -78 - 20 °C

2.1: 83 percent / ethyldiisopropylamine; KI / 1,2-dimethoxy-ethane / 3 h / Heating

3.1: 81 percent / trimethylamine oxide dihydrate; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

4.1: aq. NaIO₄ / diethyl ether / 3 h / 0 °C

5.1: NaH / toluene

5.2: 1.96 g / toluene / 2 h / 0 °C

With sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; sodium hydride; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; water; toluene; tert-butyl alcohol; 5.2: Horner-Emmons reaction;
DOI:10.1021/jm0302086

Reference yield:

: 616890-44-9
(2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(dibenzylamino)butan-1-ol

: 616890-48-3
benzyl (2E,4S,5R)-5-(dibenzylamino)-7-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)hept-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 4.87 g / tetrahydrofuran / -78 - 20 °C

3.1: 83 percent / ethyldiisopropylamine; KI / 1,2-dimethoxy-ethane / 3 h / Heating

4.1: 81 percent / trimethylamine oxide dihydrate; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

5.1: aq. NaIO₄ / diethyl ether / 3 h / 0 °C

6.1: NaH / toluene

6.2: 1.96 g / toluene / 2 h / 0 °C

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; trimethylamine-N-oxide; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 6.2: Horner-Emmons reaction;
DOI:10.1021/jm0302086