phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside
• CAS No.: 76404-29-0
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306

Synonyms:phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside

Chemical Property of phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside

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Technology Process of phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside

There total 4 articles about phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside 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%

3,4-di-O-acetyl-D-rhamnal (76739-66-7) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 4-O-acetyl-6-deoxy-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside (71978-92-2,76404-29-0)

Guidance literature:

With tin(IV) chloride;

DOI:10.1016/S0040-4039(00)88561-5

Reference yield: 91.0%

3,4-di-O-acetyl-6-deoxy-L-glucal (34819-86-8) + benzyl alcohol (100-51-6,185532-71-2) → phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside (76404-29-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

Reference yield: 85.0%

3,4-di-O-acetyl-L-rhamnal (115888-74-9) + benzyl alcohol (100-51-6,185532-71-2) → phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside (76404-29-0)

Guidance literature:

With pentafluorophenylboronic acid; In nitromethane; at 20 ℃; for 2h; stereoselective reaction;

DOI:10.3762/bjoc.15.125

upstream raw materials:

3,4-di-O-acetyl-D-rhamnal

benzyl alcohol

3,4-di-O-acetyl-6-deoxy-L-glucal

3,4-di-O-acetyl-L-rhamnal

Downstream raw materials:

(2R,3S)-6-Benzyloxy-2-methyl-3,6-dihydro-2H-pyran-3-ol

Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

4,6-diiodo-2,3-dimethoxy-5-methylphenyl 2-O-acetyl-6-deoxy-4-O-<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-α-L-mannopyranoside

4-[(2S,3R,4R,5S,6S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy]-5,6-dimethoxy-2-methyl-isophthalic acid dimethyl ester

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