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

Base Information

Chemical Name:Methyl 6-(benzyloxycarbonylamino)-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-octo-7-enofuranoside
CAS No.:262423-13-2
Molecular Formula:C₂₀H₂₇NO₆
Molecular Weight:377.437
Hs Code.:

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

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Chemical Property of Methyl 6-(benzyloxycarbonylamino)-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-octo-7-enofuranoside

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Technology Process of Methyl 6-(benzyloxycarbonylamino)-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-octo-7-enofuranoside

There total 1 articles about Methyl 6-(benzyloxycarbonylamino)-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-octo-7-enofuranoside 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: 69.0%

: 262423-12-1
Methyl 6-(benzyloxycarbonylamino)-5,6-dideoxy-2,3-O-isopropylidene-L-glycero-α-L-talo-octofuranoside

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

Guidance literature:: With 1H-imidazole; iodine; chloro-diphenylphosphine; In toluene; acetonitrile; at 90 ℃; for 4h;
DOI:10.1039/a907228d

Reference yield: 99.0%

: 100-39-0
benzyl bromide

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

: 262423-14-3
Methyl 6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-oct-7-enofuranoside

Guidance literature:: Methyl 6-(benzyloxycarbonylamino)-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-octo-7-enofuranoside; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 23 ℃; for 1h;

benzyl bromide; In tetrahydrofuran; at 23 ℃; for 12h;
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

: 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

Guidance literature:: Multi-step reaction with 3 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

With oxalyl dichloride; borane; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Metallation / 1.2: Alkylation / 2.1: Addition / 2.2: Oxidation / 3.1: Oxidation;
DOI:10.1039/a907228d