methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

Base Information

Chemical Name:methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside
CAS No.:359765-18-7
Molecular Formula:C₂₁H₃₀O₇
Molecular Weight:394.465
Hs Code.:

Synonyms:methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

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Chemical Property of methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

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Technology Process of methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

There total 1 articles about methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside 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: 59.7%

: 3970-20-5
allyl chloromethyl ether

: 201788-59-2
methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,4-furanoside

: 359765-18-7
methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

: methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptofuranoside

Guidance literature:: With magnesium; In tetrahydrofuran; at -30 - 20 ℃; for 14h;
DOI:10.1016/S0008-6215(01)00103-3

Reference yield: 80.5%

: 100-39-0
benzyl bromide

: 359765-18-7
methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

: 359765-20-1
methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at -10 - 20 ℃; for 3h;
DOI:10.1016/S0008-6215(01)00103-3

Reference yield:

: 359765-18-7
methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

: 359765-22-3
(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 80.5 percent / NaH / dimethylformamide / 3 h / -10 - 20 °C

2: 67.8 percent / 1,4-diazabicyclo[2.2.2]octane / Wilkinson's catalyst / ethanol; hexane; H₂O / 4 h / Heating

3: 76.5 percent / Swern reagent

With 1,4-diaza-bicyclo[2.2.2]octane; swern reagent; sodium hydride; Wilkinson's catalyst; In ethanol; hexane; water; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1016/S0008-6215(01)00103-3