5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

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Chemical Name:5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
CAS No.:220645-70-5
Molecular Formula:C₃₆H₄₁NO₁₀
Molecular Weight:647.722
Hs Code.:

Synonyms:5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

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Technology Process of 5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

There total 6 articles about 5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-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: 90.0%

: 220645-89-6
5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-phthalimido-β-D-glucopyranoside

: 220645-70-5
5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With 3 A molecular sieve; sodium cyanoborohydride; trifluoroacetic acid; In N,N-dimethyl-formamide; a) 0 deg C, 1.5 h, b) RT, 48 h;
DOI:10.1021/ja982232s

Reference yield:

: 10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 220645-70-5
5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / BF₃*Et₂O / CH₂Cl₂

2: 99 percent / NaOMe, MeOH / 6 h / Ambient temperature

3: 81 percent / 10-camphorsulfonic acid / acetonitrile / 2 h / Ambient temperature

4: 1.) NaH, 2.) Bu₄NI / 1.) DMF, 10 min, 2.) DMF, 0 deg C, 3 h

5: 90 percent / NaCNBH₃, 3 Angstroem molecular sieves, trifluoroacetic acid / dimethylformamide / a) 0 deg C, 1.5 h, b) RT, 48 h

With methanol; 3 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja982232s

Reference yield:

: 4547-43-7
methyl 6-hydroxycaproate

: 220645-70-5
5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / BF₃*Et₂O / CH₂Cl₂

2: 99 percent / NaOMe, MeOH / 6 h / Ambient temperature

3: 81 percent / 10-camphorsulfonic acid / acetonitrile / 2 h / Ambient temperature

4: 1.) NaH, 2.) Bu₄NI / 1.) DMF, 10 min, 2.) DMF, 0 deg C, 3 h

5: 90 percent / NaCNBH₃, 3 Angstroem molecular sieves, trifluoroacetic acid / dimethylformamide / a) 0 deg C, 1.5 h, b) RT, 48 h

With methanol; 3 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja982232s