1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol

Base Information

• Chemical Name: 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol
• CAS No.: 137964-64-8
• Molecular Formula: C₄₈H₆₈O₁₂Si
• Molecular Weight: 865.146

Synonyms:1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol

Chemical Property of 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol

Chemical Property:

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Technology Process of 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol

There total 7 articles about 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol 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: 67.0%

(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-heptonate (137945-87-0) → 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol (137964-64-8)

Guidance literature:

With pyridine; In toluene; 1) -45 deg C, 1 h, 2) 0 deg C, 30 min;

DOI:10.1021/jo00041a017

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (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) → 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol (137964-64-8)

Guidance literature:

Multi-step reaction with 6 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: 67 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 67 percent / pyridine / toluene / 1) -45 deg C, 1 h, 2) 0 deg C, 30 min

With tetrahydrofuran; pyridine; 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; toluene; acetonitrile;

DOI:10.1021/jo00041a017

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-oct-1-enitol (137964-64-8)

Guidance literature:

Multi-step reaction with 5 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: 67 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 67 percent / pyridine / toluene / 1) -45 deg C, 1 h, 2) 0 deg C, 30 min

With tetrahydrofuran; pyridine; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; borane; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrachloromethane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo00041a017

upstream raw materials:

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

2,3,5,6-di-O-isopropylidene-D-mannofuranose

(2-trimethylethylsilylethoxy)methyl chloride

(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl][(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

Downstream raw materials:

methyl (1-O-acetyl-3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside)

methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl (3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside)

methyl (1,3-dideoxy-1-iodo-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside)

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