methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside
• CAS No.: 808741-20-0
• Molecular Formula: C₇₆H₉₄O₁₉
• Molecular Weight: 1311.57

Synonyms:methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside

Chemical Property of methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside

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Technology Process of methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside

There total 9 articles about methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside 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: 89.0%

pivaloyl chloride (3282-30-2) + methyl 2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside (808741-19-7) → methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside (808741-20-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ja047194t

Reference yield:

pivaloyl chloride (3282-30-2) → methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside (808741-20-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

2.1: 1-(phenylsulfonyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3A / CH₂Cl₂ / 0.5 h / -60 °C

2.2: 80 percent / trifluoromethanesulfonic anhydride / CH₂Cl₂ / 6 h / -78 °C

3.1: 85 percent / camphorsulfonic acid; neopentyl glycol / CH₂Cl₂ / 16 h / 20 °C

4.1: 88 percent / DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

5.1: 1-(phenylsulfonyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3A / CH₂Cl₂ / 0.5 h / -60 °C

5.2: 77 percent / trifluoromethanesulfonic anhydride / CH₂Cl₂ / 6 h / -78 °C

6.1: 87 percent / camphorsulfonic acid; neopentyl glycol / CH₂Cl₂ / 18 h / 45 °C

7.1: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

With dmap; 1-(phenylsulfonyl)piperidine; 3 A molecular sieve; camphor-10-sulfonic acid; triethylamine; 2,2-Dimethyl-1,3-propanediol; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;

DOI:10.1021/ja047194t

Reference yield:

methyl β-xylopyranosyl-(1→4)-β-D-mannopyranoside (154125-79-8) → methyl 2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside (808741-20-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 89 percent / camphorsulfonic acid; neopentyl glycol / CH₂Cl₂ / 12 h / 20 °C

2.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

3.1: 1-(phenylsulfonyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3A / CH₂Cl₂ / 0.5 h / -60 °C

3.2: 80 percent / trifluoromethanesulfonic anhydride / CH₂Cl₂ / 6 h / -78 °C

4.1: 85 percent / camphorsulfonic acid; neopentyl glycol / CH₂Cl₂ / 16 h / 20 °C

5.1: 88 percent / DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

6.1: 1-(phenylsulfonyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3A / CH₂Cl₂ / 0.5 h / -60 °C

6.2: 77 percent / trifluoromethanesulfonic anhydride / CH₂Cl₂ / 6 h / -78 °C

7.1: 87 percent / camphorsulfonic acid; neopentyl glycol / CH₂Cl₂ / 18 h / 45 °C

8.1: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

With dmap; 1-(phenylsulfonyl)piperidine; 3 A molecular sieve; camphor-10-sulfonic acid; triethylamine; 2,2-Dimethyl-1,3-propanediol; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;

DOI:10.1021/ja047194t

upstream raw materials:

pivaloyl chloride

methyl 2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-pivaloyl-β-D-mannopyranoside

methyl β-xylopyranosyl-(1→4)-β-D-mannopyranoside

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

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