1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

Base Information

Chemical Name:1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside
CAS No.:688800-17-1
Molecular Formula:C₃₉H₄₂O₉
Molecular Weight:654.757
Hs Code.:

Synonyms:1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

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Chemical Property of 1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

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Technology Process of 1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

There total 12 articles about 1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside 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: 96.0%

: 1021393-74-7
3,4,6,7-tetra-O-benzyl-2-O-acetyl-D-glycero-α-D-manno-heptapyranoside

: 108-24-7
acetic anhydride

: 688800-17-1
1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: With pyridine; at 20 ℃; for 2h;
DOI:10.1002/anie.200704262

Reference yield: 60.0%

: 108-24-7
acetic anhydride

: 688800-15-9
methyl 3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

: 688800-17-1
1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: With sulfuric acid; acetic acid; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2004.02.017

Reference yield:

: 57783-73-0,79218-74-9,81561-89-9,86172-90-9,79218-87-4
methyl 3,4-di-O-benzyl-α-D-mannopyranoside

: 688800-17-1
1,2-di-O-acetyl-3,4,6,7-tetra-O-benzyl-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 82 percent / imidazole / CH₂Cl₂ / 1 h

2: 73 percent / NaH / tetrahydrofuran / 4 h

3: 74 percent / n-Bu₄NF / tetrahydrofuran / 1 h

4: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 1.3 g / diethyl ether / 0.5 h / -40 °C

6: K₂CO₃; K₃Fe(CN)6; (DHQ)2PYR / OsO₄ / 2-methyl-propan-2-ol; H₂O / 6 h / 0 °C

7: 0.71 g / PPTS / 4 h

8: 65 percent / PPTS / methanol / 6 h

9: 0.55 g / NaH / tetrahydrofuran / 12 h

10: 70 percent / DDQ / CH₂Cl₂; H₂O / 3 h

11: 60 percent / acetic acid; sulfuric acid / 1 h / 0 °C

With 1H-imidazole; oxalyl dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); sulfuric acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 4: Swern oxidation / 6: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tet.2004.02.017