methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside
CAS No.:1401426-99-0
Molecular Formula:C₂₅H₄₁IO₆Si
Molecular Weight:592.587
Hs Code.:

Synonyms:methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside

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Chemical Property of methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside

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Technology Process of methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside

There total 4 articles about methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside 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: 94.0%

: 1401426-98-9
methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

: 3282-30-2
pivaloyl chloride

: 1401426-99-0
methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside

Guidance literature:: With dmap; In 1,2-dichloro-ethane; at 50 ℃; for 1h; Inert atmosphere; Sealed tube;
DOI:10.1021/ja307207q

Reference yield:

: 76419-48-2
methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

: 1401426-99-0
methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: acetic acid / water / 1 h / 80 °C / Inert atmosphere; Sealed tube

2: 1H-imidazole; triphenylphosphine; iodine / dichloromethane; toluene / 1.75 h / 45 °C / Inert atmosphere

3: 1H-imidazole / dichloromethane / 4.5 h / 0 - 20 °C / Inert atmosphere

4: dmap / 1,2-dichloro-ethane / 1 h / 50 °C / Inert atmosphere; Sealed tube

With 1H-imidazole; dmap; iodine; acetic acid; triphenylphosphine; In dichloromethane; water; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ja307207q

Reference yield:

: 198200-37-2
methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

: 1401426-99-0
methyl 2-O-t-butyldimethylsilyloxy-3-O-benzyl-4-O-pivaloyl-6-deoxy-6-iodo-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 4.5 h / 0 - 20 °C / Inert atmosphere

2: dmap / 1,2-dichloro-ethane / 1 h / 50 °C / Inert atmosphere; Sealed tube

With 1H-imidazole; dmap; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja307207q