Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester

Base Information

• Chemical Name: Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester
• CAS No.: 102794-45-6
• Molecular Formula: C₃₀H₃₄O₇
• Molecular Weight: 506.596

Synonyms:Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester

Chemical Property of Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester

There total 1 articles about Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester 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:

Carbonic acid allyl ester (2S,3R,4R)-4-allyloxy-2,3,5-tris-benzyloxy-pentyl ester (102794-46-7) → Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester (102794-45-6)

Guidance literature:

With water; mercury dichloride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; Multistep reaction;

DOI:10.1016/S0040-4039(01)80849-2

Reference yield: 85.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose (112929-24-5,112929-25-6) + Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester (102794-45-6) → 4-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-D-glucopyranosyl)-1-O-allyloxycarbonyl-2,3,5-tri-O-benzyl-D-ribitol (112929-27-8)

Guidance literature:

With 5A molecular sieve; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -35 ℃; for 16h;

Reference yield: 5.0%

3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide (104655-87-0) + Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester (102794-45-6) → tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one (76548-23-7,10163-09-4) + 4-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-D-glucopyranosyl)-1-O-allyloxycarbonyl-2,3,5-tri-O-benzyl-D-ribitol (112929-27-8)

Guidance literature:

With mercury(II) cyanide; In dichloromethane; for 7h; Ambient temperature;

upstream raw materials:

Carbonic acid allyl ester (2S,3R,4R)-4-allyloxy-2,3,5-tris-benzyloxy-pentyl ester

Downstream raw materials:

tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one

4-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-D-glucopyranosyl)-1-O-allyloxycarbonyl-2,3,5-tri-O-benzyl-D-ribitol

(2S,3R,4R)-2,3,5-tri-O-benzyl-pentane-1,4-diol

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