(E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester
• CAS No.: 440122-32-7
• Molecular Formula: C₃₈H₄₂O₇
• Molecular Weight: 610.747

Synonyms:(E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester

Chemical Property of (E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester

Chemical Property:

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Technology Process of (E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester

There total 2 articles about (E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl 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: 56.0%

Phenylselenyl chloride (5707-04-0) + ethyl 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)acetate (82598-90-1) → (E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester (440122-32-7) + (S)-Phenylselanyl-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (440122-31-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -60 ℃;

DOI:10.1021/jo0255227

Reference yield:

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene (82659-59-4) → (E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester (440122-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / O₃

2: 56 percent / LHMDS / tetrahydrofuran / -78 - -60 °C

With ozone; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jo0255227

Reference yield: 71.0%

Phenylselenyl chloride (5707-04-0) + (E)-4,5,6,8-tetra-O-benzyl-7-hydroxy-D-mannooct-2-enoic acid ethyl ester (440122-32-7) → (S)-Phenylselanyl-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (440122-31-6) + (R)-Phenylselanyl-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (440122-33-8)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 144h;

DOI:10.1021/jo0255227

upstream raw materials:

Phenylselenyl chloride

ethyl 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)acetate

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene

Downstream raw materials:

(S)-Phenylselanyl-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

(R)-Phenylselanyl-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

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