benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside

Base Information

• Chemical Name: benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside
• CAS No.: 117996-84-6
• Molecular Formula: C₂₉H₃₃NO₆
• Molecular Weight: 491.584

Synonyms:benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside

Chemical Property of benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside

Chemical Property:

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Technology Process of benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside

There total 2 articles about benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside 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: 49.4%

(1S,2R,4R,5R)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-methyl-3-oxa-6-azabicyclo<3.2.0>heptan-7-one + benzyl alcohol (100-51-6,185532-71-2) → benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-β-D-ribofuranoside (117996-79-9) + benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside (117996-84-6)

Guidance literature:

With hydrogenchloride; 5 h, 0 deg C, then 15 h, room temperature;

DOI:10.1271/bbb1961.52.2027

Reference yield: 7.8%

(1S,2R,4R,5R)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-methyl-3-oxa-6-azabicyclo<3.2.0>heptan-7-one + benzyl alcohol (100-51-6,185532-71-2) → (1S,2R,4R,5R)-4-benzyloxy-6-(2,4-dimethoxybenzyl)-2-methyl-3-oxa-6-azabicyclo<3.2.0>heptan-7-one + benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-β-D-ribofuranoside (117996-79-9) + benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside (117996-84-6)

Guidance literature:

With hydrogenchloride; at 0 ℃; for 15h;

DOI:10.1271/bbb1961.52.2027

Reference yield: 80.4%

benzyl 3-C-benzyloxycarbonyl-2-(2,4-dimethoxybenzylamino)-2,3,5-trideoxy-α-D-ribofuranoside (117996-84-6) → benzyl 2-amino-3-C-benzyloxycarbonyl-2,3,5-trideoxy-α-D-ribofuranoside (117996-81-3)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetone; for 0.0833333h; Ambient temperature;

DOI:10.1271/bbb1961.52.2027

upstream raw materials:

benzyl alcohol

Downstream raw materials:

benzyl 2-amino-3-C-benzyloxycarbonyl-2,3,5-trideoxy-α-D-ribofuranoside

benzyl 2-acetamido-3-C-formyl-2,3,5-trideoxy-α-D-ribofuranoside

benzyl 2-benzamido-3-C-(3-chlorobenzoyldioxycarbonyl)-2,3,5-trideoxy-α-D-ribofuranoside

benzyl 2-amino-3-C-hydroxymethyl-2,3,5-trideoxy-α-D-ribofuranoside

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