(2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene

Base Information

Chemical Name:(2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene
CAS No.:147910-01-8
Molecular Formula:C₅₀H₉₃NO₄Si
Molecular Weight:800.378
Hs Code.:

Synonyms:(2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene

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Chemical Property of (2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene

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Technology Process of (2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene

There total 7 articles about (2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene 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:

: 3587-60-8
Benzyloxymethyl chloride

: 147910-01-8
(2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene

Guidance literature:: Multi-step reaction with 7 steps

1: 73 percent / iPr₂NEt / CH₂Cl₂ / 8 h / 0 deg C to RT

2: 1) Ph₃P, 2) H₂O / 1) benzene, 45 deg C, 30 min, 2) 45 deg C, 11 h

3: Et₃N, DMAP / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) RT, 5 h

4: 82 percent / LiI, NaBH₄ / tetrahydrofuran / 3 h / 35 - 40 °C

5: 1) NaH / 1) THF, RT, 45 min, 2) THF, RT, 45 min

6: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 to -50 deg C, 15 min, 2a) CH₂Cl₂, -60 deg C, 10 min, 2b) to RT, 1 h

7: 1) n-BuLi / 1) THF, hexane, -10 deg C, 2 min, 2) -10 to +20 deg C, 2 h

With dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; water; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; In tetrahydrofuran; dichloromethane;

Reference yield:

: 147909-94-2
(2S,3R)-2-Amino-3-benzyloxymethoxy-succinic acid diethyl ester

: 147910-01-8
(2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N, DMAP / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) RT, 5 h

2: 82 percent / LiI, NaBH₄ / tetrahydrofuran / 3 h / 35 - 40 °C

3: 1) NaH / 1) THF, RT, 45 min, 2) THF, RT, 45 min

4: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 to -50 deg C, 15 min, 2a) CH₂Cl₂, -60 deg C, 10 min, 2b) to RT, 1 h

5: 1) n-BuLi / 1) THF, hexane, -10 deg C, 2 min, 2) -10 to +20 deg C, 2 h

With dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; lithium iodide; In tetrahydrofuran; dichloromethane;

Reference yield:

: 147909-93-1
diethyl (2R,3S)-2-azido-3-(benzyloxymethoxy)butane-1,4-dioate

: 147910-01-8
(2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene

Guidance literature:: Multi-step reaction with 6 steps

1: 1) Ph₃P, 2) H₂O / 1) benzene, 45 deg C, 30 min, 2) 45 deg C, 11 h

2: Et₃N, DMAP / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) RT, 5 h

3: 82 percent / LiI, NaBH₄ / tetrahydrofuran / 3 h / 35 - 40 °C

4: 1) NaH / 1) THF, RT, 45 min, 2) THF, RT, 45 min

5: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 to -50 deg C, 15 min, 2a) CH₂Cl₂, -60 deg C, 10 min, 2b) to RT, 1 h

6: 1) n-BuLi / 1) THF, hexane, -10 deg C, 2 min, 2) -10 to +20 deg C, 2 h

With dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; water; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium iodide; In tetrahydrofuran; dichloromethane;