1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol

Base Information

• Chemical Name: 1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol
• CAS No.: 850534-40-6
• Molecular Formula: C₃₄H₅₈O₈Si₂
• Molecular Weight: 651.001

Synonyms:1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol

Chemical Property of 1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol

Chemical Property:

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Technology Process of 1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol

There total 2 articles about 1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol 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: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,5-di-O-(p-methoxybenzyl)-D-mannitol (301298-48-6) → 1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol (850534-40-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/jo048308m

Reference yield:

1,3:4,6-di-O-benzylidene-2,5-bis-O-(p-methoxybenzyl)-D-mannitol → 1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol (850534-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / aq. HCl / methanol; hexane / 11 h / 20 °C

2: 93 percent / imidazole / dimethylformamide; CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo048308m

Reference yield: 85.0%

1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol (850534-40-6) → 3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propionaldehyde

Guidance literature:

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1021/jo048308m

upstream raw materials:

tert-butyldimethylsilyl chloride

2,5-di-O-(p-methoxybenzyl)-D-mannitol

Downstream raw materials:

1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

1-(6-{(1R)-1-[(4-methoxyphenyl)methoxy]-2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))(2R,3R)-3-[(phenylmethoxy)methoxy]butan-2-ol

(1R,2R)-1-[(6-{(1S)-1-[(4-methoxyphenyl)methoxy]-3,3-dimethyl-2-oxopent-4-enyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl]-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

(1R,5R,6R)-1-{(1R)-1-[(phenylmethoxy)methoxy]ethyl}-5-hydroxy-6-[(4-methoxyphenyl)methoxy]-3-oxo-7-(1,1,2,2-tetramethyl-1-silapropoxy)heptyl 2,2-dimethylpropanoate

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