methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside
CAS No.:507485-64-5
Molecular Formula:C₄₄H₅₀O₁₂
Molecular Weight:770.874
Hs Code.:

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

There total 11 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-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: 72.0%

: 100-39-0
benzyl bromide

: 507485-63-4
methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

: 507485-64-5
methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

Guidance literature:: methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside; With ozone; In dichloromethane; at -78 ℃;

With sodium chlorite; sodium dihydrogenphosphate; In water; tert-butyl alcohol; at 20 ℃;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; potassium hydrogencarbonate; In N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

Reference yield:

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

: 507485-64-5
methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: 80 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂

2.1: sodium / methanol / 8 h / 20 °C

2.2: p-toluenesulfonic acid / acetone / 20 °C

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂

4.1: lithium triethylborohydride / tetrahydrofuran

5.1: pyridine / 20 °C

6.1: 342.7 mg / acetic acid / 2 h / 60 °C

7.1: 91 percent / triethylamine; dimethylaminopyridine / CH₂Cl₂ / 20 °C

8.1: 93 percent / camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 0 °C

9.1: NaOH / ethanol / 72 h

10.1: 84 percent / toluenesulfonic acid / methanol / 0.25 h / 20 °C

11.1: ozone / CH₂Cl₂ / -78 °C

11.2: NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; various solvent(s); H₂O / 20 °C

11.3: 72 percent / tetrabutylammonium iodide; potassium hydrogen carbonate / dimethylformamide

With pyridine; dmap; sodium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; o-toluenesulfonic acid; camphor-10-sulfonic acid; sodium; lithium triethylborohydride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

Reference yield:

: (2R,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-tetrahydro-1,5,7-trioxa-benzocyclohepten-3-one

: 507485-64-5
methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium triethylborohydride / tetrahydrofuran

2.1: pyridine / 20 °C

3.1: 342.7 mg / acetic acid / 2 h / 60 °C

4.1: 91 percent / triethylamine; dimethylaminopyridine / CH₂Cl₂ / 20 °C

5.1: 93 percent / camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 0 °C

6.1: NaOH / ethanol / 72 h

7.1: 84 percent / toluenesulfonic acid / methanol / 0.25 h / 20 °C

8.1: ozone / CH₂Cl₂ / -78 °C

8.2: NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; various solvent(s); H₂O / 20 °C

8.3: 72 percent / tetrabutylammonium iodide; potassium hydrogen carbonate / dimethylformamide

With pyridine; dmap; sodium hydroxide; o-toluenesulfonic acid; camphor-10-sulfonic acid; lithium triethylborohydride; ozone; acetic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F