4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol

Base Information

• Chemical Name: 4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol
• CAS No.: 440360-41-8
• Molecular Formula: C₂₈H₃₁IO₈
• Molecular Weight: 622.454

Synonyms:4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol

Chemical Property of 4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol

Chemical Property:

Purity/Quality:

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Technology Process of 4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol

There total 2 articles about 4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol 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: 78.0%

Acetic acid (1S,2R,3R)-2-acetoxy-1-[(1R,2R)-2-acetoxy-1-benzyloxy-3-(toluene-4-sulfonyloxy)-propyl]-3-benzyloxy-pent-4-ynyl ester (440360-51-0) → 4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol (440360-41-8)

Guidance literature:

With sodium iodide; In acetone; Heating;

DOI:10.1021/jo0111107

Reference yield:

4,5,7-tri-O-acetyl-1,2-dideoxy-3,6-bis-O-(phenylmethyl)-8-p-toluensulfonyl-D-glycero-D-talo-oct-1-ynitol (440360-50-9) → 4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol (440360-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine / 20 °C

2: 78 percent / NaI / acetone / Heating

With pyridine; sodium iodide; In acetone;

DOI:10.1021/jo0111107

Reference yield: 80.0%

4,5,7-tri-O-acetyl-1,2,8-trideoxy-8-iodo-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol (440360-41-8) → 1,2-dideoxy-4,5:7,8-bis-O-(1-methylethylidene)-1-phenyl-D-glycero-D-galacto-oct-1-ynitol (354137-28-3) + 4,5,7-tri-O-acetyl-1,2,8-trideoxy-3,6-bis-O-(phenylmethyl)-D-glycero-D-talo-oct-1-ynitol

Guidance literature:

With triethyl borane; triphenylstannane; In toluene; at -78 ℃;

DOI:10.1021/jo0111107

upstream raw materials:

Acetic acid (1S,2R,3R)-2-acetoxy-1-[(1R,2R)-2-acetoxy-1-benzyloxy-3-(toluene-4-sulfonyloxy)-propyl]-3-benzyloxy-pent-4-ynyl ester

4,5,7-tri-O-acetyl-1,2-dideoxy-3,6-bis-O-(phenylmethyl)-8-p-toluensulfonyl-D-glycero-D-talo-oct-1-ynitol

Downstream raw materials:

1,2-dideoxy-4,5:7,8-bis-O-(1-methylethylidene)-1-phenyl-D-glycero-D-galacto-oct-1-ynitol

1,2-dideoxy-1-phenyl-3,6-bis-O-(phenylmethyl)-D-glycero-D-galacto-oct-1-ynitol

1,2-dideoxy-4,5:7.8-bis-O-(1-methylethylidene)-1-phenyl-3,6-bis-O-(phenylmethyl)-D-blycero-D-galacto-oct-1-ynitol

1,2-dideoxy-1-phenyl-3,6-bis-O-(phenylmethyl)-8-p-tolyenesulfonyl-D-glycero-D-galacto-oct-1-ynitol

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