Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 698999-98-3
• Molecular Formula: C₂₀H₂₁IO₄
• Molecular Weight: 452.289

Synonyms:Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester

There total 2 articles about Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl 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: 100.0%

benzoyl chloride (98-88-4) + (3-O-benzyl-2-deoxy-α-D-erythro-pentofuranosyl)iodomethane (116558-42-0) → Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester (698999-98-3)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2004.03.091

Reference yield:

(R)-4-((R)-1-(benzyloxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane (87604-54-4) → Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester (698999-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / Ag(sym-coll)2ClO₄; I₂ / acetonitrile; H₂O / 1 h / 20 °C

2: 100 percent / DMAP / pyridine / 2 h / 20 °C

With dmap; Ag(sym-coll)2ClO₄; iodine; In pyridine; water; acetonitrile;

DOI:10.1016/j.tetlet.2004.03.091

Reference yield: 43.0%

Benzoic acid (2R,3S,5S)-3-benzyloxy-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester (698999-98-3) → Benzoic acid (2R,3S)-3-benzyloxy-5-methylene-tetrahydro-furan-2-ylmethyl ester

Guidance literature:

With potassium tert-butylate; In dichloromethane;

DOI:10.1016/j.tetlet.2004.03.091

upstream raw materials:

benzoyl chloride

(3-O-benzyl-2-deoxy-α-D-erythro-pentofuranosyl)iodomethane

(R)-4-((R)-1-(benzyloxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane

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