methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

Base Information

Chemical Name:methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside
CAS No.:294637-42-6
Molecular Formula:C₅₈H₆₅ClO₁₁
Molecular Weight:973.601
Hs Code.:

Synonyms:methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

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Chemical Property of methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

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Technology Process of methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

There total 13 articles about methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-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: 99.0%

: 107-08-4
1-iodo-propane

: 294637-41-5
methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

: 294637-42-6
methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 3h;
DOI:10.1021/ja0008665

Reference yield:

: 294637-63-1
(2R,3S,4R)-2-Benzyloxymethyl-4-(4-bromo-benzyloxy)-3-(4-chloro-benzyloxy)-3,4-dihydro-2H-pyran

: 294637-42-6
methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / DMDO

2: 88 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

3: tBuONa; Pd₂(dba)3; (o-biphenyl)P(tBu)2 / toluene / 16 h / 80 °C

4: 0.181 g / SnCl₄ / heptane / 0.5 h / 20 °C

5: 99 percent / NaH / dimethylformamide; various solvent(s) / 3 h

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; tin(IV) chloride; sodium hydride; johnphos; sodium t-butanolate; In n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Addition / 1: Etherification / 2: glycosylation / 3: Substitution / 4: acidolysis / 5: Alkylation;
DOI:10.1021/ja0008665

Reference yield:

: 294637-62-0
[(2R,3S,4R)-4-(4-Bromo-benzyloxy)-3-(4-chloro-benzyloxy)-3,4-dihydro-2H-pyran-2-ylmethoxy]-triisopropyl-silane

: 294637-42-6
methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-3-O-propyl-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: TBAF; HOAc

1.2: 86 percent / NaH / dimethylformamide; various solvent(s) / 0.5 h / 20 °C

2.1: 86 percent / DMDO

3.1: 88 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

4.1: tBuONa; Pd₂(dba)3; (o-biphenyl)P(tBu)2 / toluene / 16 h / 80 °C

5.1: 0.181 g / SnCl₄ / heptane / 0.5 h / 20 °C

6.1: 99 percent / NaH / dimethylformamide; various solvent(s) / 3 h

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tin(IV) chloride; sodium hydride; acetic acid; johnphos; sodium t-butanolate; In n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: acidolysis / 1.2: Etherification / 2.1: Addition / 2.2: Etherification / 3.1: glycosylation / 4.1: Substitution / 5.1: acidolysis / 6.1: Alkylation;
DOI:10.1021/ja0008665