-5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid

Base Information

• Chemical Name: -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid
• CAS No.: 136029-31-7
• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.411

Synonyms:-5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid

Chemical Property of -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid

Chemical Property:

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Technology Process of -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid

There total 12 articles about -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid 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: 100.0%

methyl -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronate (136029-30-6,136029-37-3) → -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid (136029-31-7)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; water; at 50 ℃; for 24h;

DOI:10.1016/S0040-4039(00)79713-9

Reference yield:

(+/-)-methyl -5-deoxy-2,3-O-isopropylidene-5-methyl-αβ-L-allo-hexofuranosid>uronate (136029-30-6,136029-37-3) → (+/-)--5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid (136029-31-7)

Guidance literature:

With potassium hydroxide; In methanol; at 50 ℃; for 24h;

DOI:10.1016/S0040-4020(01)91030-0

Reference yield:

benzyl bromomethyl ether (17690-16-3) → -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronic acid (136029-31-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) LiN(SiMe₃)2 / 1) hexane, THF, -60 deg C, 2 h, 2) up to -10 deg C, 30 min

2: 93 percent / K₂CO₃ / methanol / 2 h / 20 °C

3: 87 percent / Amberlist 15 / CCl₄ / 24 h / 20 °C

4: 1 N aq. KOH / methanol / 24 h / 50 °C

With potassium hydroxide; Amberlist 15; potassium carbonate; lithium hexamethyldisilazane; In methanol; tetrachloromethane;

DOI:10.1016/S0040-4020(01)91030-0

upstream raw materials:

methyl -5-deoxy-2,3-O-isopropylidene-5-methyl-β-L-allo-hexofuranosid>uronate

benzyl bromomethyl ether

(1S,2S,6S,7R,10R)-4,4,10-Trimethyl-3,5,8,11-tetraoxa-tricyclo[5.3.1.0^2,6]undecan-9-one

(1R,4R,5S,6S,7S)-4-exo<(benzyloxy)methyl>-6-exo,7-exo-(isopropylidenedioxy)-4-endo-methyl-2,8-dioxabicyclo<3.2.1>octan-3-one

Downstream raw materials:

C₂₂H₃₀O₉

methyl 6-O-benzyl-5-<<(benzyloxy)carbonyl>amino>-5-deoxy-2,3-O-isopropylidene-5-methyl-α-D-talo-hexofuranoside

methyl 6-O-benzyl-5-deoxy-5-isocyanato-2,3-O-isopropylidene-5-methyl-α-D-talo-hexofuranoside

C₂₂H₃₀O₉

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