Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

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Chemical Name:Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate
CAS No.:180776-35-6
Molecular Formula:C₃₃H₄₄N₂O₉
Molecular Weight:612.72
Hs Code.:

Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

Synonyms:Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

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Chemical Property of Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

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Technology Process of Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

There total 6 articles about Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate 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: 95.0%

: (E/Z)-Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-α-L-talo-dec-8-enofuranosid}uronate

: 180776-35-6
Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

Guidance literature:: With [Rh((R,R)-DIPAMP)(COD)]BF₄; hydrogen; In methanol; at 23 ℃; for 10h; under 2585.7 Torr;
DOI:10.1021/jo960670g

Reference yield:

: 85992-74-1
2-Acetylamino-2-(diethoxyphosphoryl)essigsaeure-ethylester

: Benzyl-[(R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-3-oxo-propyl]-carbamic acid benzyl ester

: 180776-35-6
Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

Guidance literature:: 2-Acetylamino-2-(diethoxyphosphoryl)essigsaeure-ethylester; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.25h;

Benzyl-[(R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-3-oxo-propyl]-carbamic acid benzyl ester; In tetrahydrofuran; at -78 ℃; for 0.5h;

With hydrogen; (R,R)-(-)-1,2-bis[(o-methoxy-phenyl)phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In methanol; at 23 ℃; for 12h; under 2585.74 Torr;
DOI:10.1039/a907228d

Reference yield:

: 262423-13-2
Methyl 6-(benzyloxycarbonylamino)-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-octo-7-enofuranoside

: 180776-35-6
Ethyl {methyl 9-acetamido-6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-D-glycero-α-L-talo-decofuranosid}uronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH; n-Bu₄NI / tetrahydrofuran / 1 h / 23 °C

1.2: 99 percent / tetrahydrofuran / 12 h / 23 °C

2.1: BH₃ / tetrahydrofuran / 1 h / 23 °C

2.2: 57 percent / NaOH; H₂O₂; H₂O / tetrahydrofuran / 1 h / 23 °C

3.1: DMSO; oxalyl chloride; diisopropylethylamine / CH₂Cl₂ / 0.5 h / -60 - -50 °C

4.1: 18-crown-6; KN(TMS)2 / tetrahydrofuran; toluene / 0.25 h / -78 °C

4.2: tetrahydrofuran / 0.5 h / -78 °C

4.3: H₂ / [Rh(COD)(R,R-DIPAMP)2]⁽¹⁺⁾BF₄^(1-) / methanol / 12 h / 23 °C / 2585.74 Torr

With oxalyl dichloride; 18-crown-6 ether; borane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: Addition / 2.2: Oxidation / 3.1: Oxidation / 4.1: Metallation / 4.2: Condensation / 4.3: Catalytic hydrogenation;
DOI:10.1039/a907228d