methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

Base Information

Chemical Name:methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside
CAS No.:497234-44-3
Molecular Formula:C₁₉H₂₉O₉P
Molecular Weight:432.408
Hs Code.:

Synonyms:methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

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Chemical Property of methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

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Technology Process of methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

There total 5 articles about methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside 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: 76.0%

: 868-85-9
Dimethyl phosphite

: 497234-42-1
methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose

: 497234-44-3
methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

: 497234-43-2
methyl (5R)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 0 ℃; for 0.5h;
DOI:10.1002/1522-2675(200209)85:9<2608::AID-HLCA2608>3.0.CO;2-F

Reference yield:

: 27954-10-5
methyl 2,3-O-isopropylidene-α-D-mannofuranoside

: 497234-44-3
methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1: PPh₃; DEAD / toluene / Heating

2: NaH / 1,2-dimethoxy-ethane; various solvent(s) / 60 °C

3: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

4: 19 percent / DBU / 0.5 h / 0 °C

With 4 A molecular sieve; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In 1,2-dimethoxyethane; dichloromethane; toluene;
DOI:10.1016/S0008-6215(03)00235-0

Reference yield:

: 161365-10-2
methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-mannofuranoside

: 497234-44-3
methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

2: 19 percent / DBU / 0.5 h / 0 °C

With 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In dichloromethane;
DOI:10.1016/S0008-6215(03)00235-0