{(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester
• CAS No.: 793733-71-8
• Molecular Formula: C₅₈H₈₁NO₇
• Molecular Weight: 904.284

Synonyms:

Chemical Property of {(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester

There total 7 articles about {(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl 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:

(4S)-4-(2'-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (223526-25-8) → {(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester (793733-71-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / DCC; 4-DMAP

2.1: TiCl₄; TMEDA; PbCl₂

3.1: Grubbs ruthenium catalyst / 60 °C

3.2: BH₃*THF; NaOOH

4.1: 98 percent / NaH

5.1: p-TsOH / methanol

With dmap; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; sodium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; lead(II) chloride; Grubbs catalyst first generation; In methanol; 2.1: Takai methylenation / 3.1: ring closing metathesis / 6.1: Swern oxidation / 7.1: Wittig reaction;

DOI:10.1016/j.tetlet.2004.07.163

Reference yield:

3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enitol (302800-64-2) → {(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester (793733-71-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / DCC; 4-DMAP

2.1: TiCl₄; TMEDA; PbCl₂

3.1: Grubbs ruthenium catalyst / 60 °C

3.2: BH₃*THF; NaOOH

4.1: 98 percent / NaH

5.1: p-TsOH / methanol

With dmap; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; sodium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; lead(II) chloride; Grubbs catalyst first generation; In methanol; 2.1: Takai methylenation / 3.1: ring closing metathesis / 6.1: Swern oxidation / 7.1: Wittig reaction;

DOI:10.1016/j.tetlet.2004.07.163

Reference yield:

(S)-4-[2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (793733-68-3) → {(Z)-(S)-1-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester (793733-71-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: TiCl₄; TMEDA; PbCl₂

2.1: Grubbs ruthenium catalyst / 60 °C

2.2: BH₃*THF; NaOOH

3.1: 98 percent / NaH

4.1: p-TsOH / methanol

With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; sodium hydride; toluene-4-sulfonic acid; lead(II) chloride; Grubbs catalyst first generation; In methanol; 1.1: Takai methylenation / 2.1: ring closing metathesis / 5.1: Swern oxidation / 6.1: Wittig reaction;

DOI:10.1016/j.tetlet.2004.07.163

upstream raw materials:

Pentadecylidene-triphenyl-λ⁵-phosphane

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitose

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol

Downstream raw materials:

(3S,4S,5R)-3-Amino-1-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-nonadecane-4,5-diol

{(1S,2S,3R)-2,3-Dihydroxy-1-[2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadecyl}-carbamic acid tert-butyl ester

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