1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose

Base Information

• Chemical Name: 1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose
• CAS No.: 1451180-26-9
• Molecular Formula: C₁₉H₃₁IO₃Si
• Molecular Weight: 462.443

Synonyms:1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose

Chemical Property of 1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose

Chemical Property:

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Technology Process of 1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose

There total 2 articles about 1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose 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: 95.0%

1,2,6-trideoxy-3-O-benzyl-6-iodo-D-glucopyranose (112430-54-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose (1451180-26-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1021/ol402021e

Reference yield:

1,2-dideoxy-3-O-benzyl-β-D-glucose (64879-36-3) → 1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose (1451180-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole; triphenylphosphine; iodine / toluene / Inert atmosphere; Reflux

2: 1H-imidazole / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere

With 1H-imidazole; iodine; triphenylphosphine; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol402021e

Reference yield: 85.0%

1,2,6-trideoxy-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-iodo-D-glucopyranose (1451180-26-9) → C19H30O3Si (1451180-27-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 1.5h; Inert atmosphere; Reflux;

DOI:10.1021/ol402021e

upstream raw materials:

1,2-dideoxy-3-O-benzyl-β-D-glucose

1,2,6-trideoxy-3-O-benzyl-6-iodo-D-glucopyranose

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₁₉H₃₀O₃Si

C₂₂H₃₄O₅Si

C₂₂H₃₄O₆Si

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