8-Methoxycarbonyloctyl4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl)-2-deoxy-3-O-benzyl-2-phthalimido-b-D-glucopyranoside

Base Information

• Chemical Name: 8-Methoxycarbonyloctyl4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl)-2-deoxy-3-O-benzyl-2-phthalimido-b-D-glucopyranoside
• CAS No.: 106445-30-1
• Molecular Formula: C51H58 N2 O18
• Molecular Weight: 987.01
• Mol file: 106445-30-1.mol

Synonyms:8-Methoxycarbonyloctyl4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl)-2-deoxy-3-O-benzyl-2-phthalimido-b-D-glucopyranoside

Chemical Property of 8-Methoxycarbonyloctyl4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl)-2-deoxy-3-O-benzyl-2-phthalimido-b-D-glucopyranoside

Chemical Property:

• PSA: 246.34000
• LogP: 3.95130

Purity/Quality:

95% ^*data from raw suppliers

8-Methoxycarbonyloctyl-2-deoxy-2-phthalimido-3-O-benzyl-4-O-(3’,4’,6’-tri-O-acetyl-2’-deoxy-2’-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 8-Methoxycarbonyloctyl4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl)-2-deoxy-3-O-benzyl-2-phthalimido-b-D-glucopyranoside

There total 8 articles about 8-Methoxycarbonyloctyl4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl)-2-deoxy-3-O-benzyl-2-phthalimido-b-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: 86.0%

8-methoxycarbonyloctyl 3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-2-phthalimido-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside (106445-29-8) → 8-methoxycarbonyloctyl 3-O-benzyl-2-deoxy-2-phthalimido-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside (106445-30-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; Ambient temperature; 1) 0 deg C, 10 min, 2) RT, 45 min;

Reference yield:

8-ethoxycarbonyloctanol (3639-34-7) → 8-methoxycarbonyloctyl 3-O-benzyl-2-deoxy-2-phthalimido-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside (106445-30-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 54 percent / silver zeolite / CH₂Cl₂ / 40 h / Ambient temperature

2: 99 percent / methanol / 0.5 h

3: 64 percent / p-TsOH*H₂O / acetonitrile / 0.83 h / Ambient temperature

4: 90 percent / 1) NaH / tetrahydrofuran / 21 h / Ambient temperature

5: 1) sodium cyanoborohydride, mol. sieves 3A, 2) TFA / 1) DMF, 15 min, RT, 2) DMF, 43 h

6: 66 percent / silver triflate, collidine / nitromethane / 1) -25 deg C, 30 min, 2) RT, 4.5 h

7: 86 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / Ambient temperature; 1) 0 deg C, 10 min, 2) RT, 45 min

With 2,3,5-trimethyl-pyridine; ammonium cerium(IV) nitrate; 3 A molecular sieve; silver zeolite; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; nitromethane; dichloromethane; water; acetonitrile;

Reference yield:

8-methoxycarbonyloctyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (106445-25-4) → 8-methoxycarbonyloctyl 3-O-benzyl-2-deoxy-2-phthalimido-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside (106445-30-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / p-TsOH*H₂O / acetonitrile / 0.83 h / Ambient temperature

2: 90 percent / 1) NaH / tetrahydrofuran / 21 h / Ambient temperature

3: 1) sodium cyanoborohydride, mol. sieves 3A, 2) TFA / 1) DMF, 15 min, RT, 2) DMF, 43 h

4: 66 percent / silver triflate, collidine / nitromethane / 1) -25 deg C, 30 min, 2) RT, 4.5 h

5: 86 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / Ambient temperature; 1) 0 deg C, 10 min, 2) RT, 45 min

With 2,3,5-trimethyl-pyridine; ammonium cerium(IV) nitrate; 3 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; nitromethane; water; acetonitrile;

upstream raw materials:

8-methoxycarbonyloctyl 3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-2-phthalimido-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside

8-ethoxycarbonyloctanol

8-methoxycarbonyloctyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

8-methoxycarbonyloctyl 2-deoxy-4,6-O-(4-methoxybenzylidene)-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

8-methoxycarbonyloctyl 4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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