(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate

Base Information

Chemical Name:(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate
CAS No.:137945-90-5
Molecular Formula:C₄₇H₆₆O₁₃Si
Molecular Weight:867.119
Hs Code.:

Synonyms:(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate

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Chemical Property of (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate

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Technology Process of (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate

There total 6 articles about (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate 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: 60.0%

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 137945-81-4
2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-heptonic acid

: 137945-90-5
(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1021/jo00041a017

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 137945-90-5
(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate

Guidance literature:: Multi-step reaction with 5 steps

1: 71 percent / n-BuLi / tetrahydrofuran; hexane / 15 h / 20 °C

2: 88 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 40 °C

3: 1) BH₃/THF, 2) 25percent H₂O₂, NaOH / 1) THF, 0 deg C to rt, 30 min, 2) THF, H₂O

4: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / Ambient temperature

5: 60 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With tetrahydrofuran; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; n-butyllithium; borane; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00041a017

Reference yield:

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 137945-90-5
(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<(trimethylsilyl)ethoxymethyl>-D-manno-heptonate

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 40 °C

2: 1) BH₃/THF, 2) 25percent H₂O₂, NaOH / 1) THF, 0 deg C to rt, 30 min, 2) THF, H₂O

3: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / Ambient temperature

4: 60 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With tetrahydrofuran; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; borane; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00041a017