4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

Base Information

Chemical Name:4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside
CAS No.:220098-51-1
Molecular Formula:C₃₇H₄₇IO₁₀Si
Molecular Weight:806.764
Hs Code.:

Synonyms:4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

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Chemical Property of 4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

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Technology Process of 4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

There total 1 articles about 4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside 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: 68.0%

: 131675-55-3
phenyl 2,4-di-O-acetyl-3-O-methyl-1-thio-α-L-rhamnopyranoside

: 153693-56-2
4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-iodo-5,6-dimethoxy-3-methyl-phenol

: 220098-51-1
4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 ℃;
DOI:10.1016/S0040-4039(98)02257-6

Reference yield: 75.0%

: 220098-51-1
4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

: 220098-52-2
4-(Hydroxymethyl)-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(98)02257-6

Reference yield:

: 220098-51-1
4-[(tert-Butyldiphenylsiloxy)methyl]-2-iodo-5,6-dimethoxy-3-methylphenyl 2,4-di-O-acetyl-6-deoxy-3-O-methyl-α-L-mannopyranoside

: 129834-75-9
4-<(6-deoxy-3-O-methyl-2,4-O,O-bis(triethylsilyl)-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoic acid chloride

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

2: 60 percent / RuCl₃*H₂O; NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / 20 °C

3: 79 percent / LiOH*H₂O; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

4: 80 percent / DMAP; pyridine / CH₂Cl₂ / 1 h / 20 °C

5: (COCl)2 / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; ruthenium trichloride; lithium hydroxide; sodium periodate; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile; 2: Sharpless oxidation;
DOI:10.1039/b006113l