(Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

Base Information

Chemical Name:(Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester
CAS No.:881015-91-4
Molecular Formula:C₅₆H₆₉NO₁₀Si
Molecular Weight:944.25
Hs Code.:

(Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

Synonyms:(Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

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Chemical Property of (Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

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Technology Process of (Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

There total 8 articles about (Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl 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: 92.0%

: 881015-90-3
(3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: 881015-91-4
(Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/jo052256z

Reference yield:

: 881015-88-9
(S)-2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-pent-4-en-1-ol

: 881015-91-4
(Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2.33 g / 2,3,5-collidine / CH₂Cl₂ / 0.33 h / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 96 percent / PS-PPh₃ / CH₂Cl₂ / 14 h / -78 - 20 °C

3.1: 92 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

With 2,3,5-trimethyl-pyridine; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 3.1: Horner-Emmons olefination;
DOI:10.1021/jo052256z

Reference yield:

: C₄₂H₄₈O₈

: 881015-91-4
(Z)-(S)-2-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 13.1 g / Et₃N*HCl; BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: 70 percent / NaHMDS / tetrahydrofuran / -78 - 20 °C

3.1: LiAlH₄ / diethyl ether / 0.25 h / 20 °C

4.1: 2.33 g / 2,3,5-collidine / CH₂Cl₂ / 0.33 h / 20 °C

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: 96 percent / PS-PPh₃ / CH₂Cl₂ / 14 h / -78 - 20 °C

6.1: 92 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

With 2,3,5-trimethyl-pyridine; lithium aluminium tetrahydride; n-butyllithium; sodium hexamethyldisilazane; triethylamine hydrochloride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 6.1: Horner-Emmons olefination;
DOI:10.1021/jo052256z