Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 226927-54-4
• Molecular Formula: C₄₇H₅₆N₆O₁₇
• Molecular Weight: 976.992

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

There total 7 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester 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%

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + methyl (2,4-diazido-2,4-dideoxy-β-D-xylopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (226927-52-2) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (226927-54-4)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ja984062p

Reference yield:

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (20672-67-7) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (226927-54-4)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSOTf / acetonitrile / -40 °C

2: NaOMe

3: 86 percent / BF₃*OEt₂, 4A molecular sieves / CH₂Cl₂ / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; In dichloromethane; acetonitrile;

DOI:10.1021/ja984062p

Reference yield:

methyl 2,4-diazido-2,4-dideoxy-β-D-xylopyranoside (226927-44-2) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3R,4S,5R)-3,5-diazido-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (226927-54-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / H₂SO₄

2: H₂NNH₂*AcOH / dimethylformamide / 50 °C

3: Cs₂CO₃ / 1,2-dichloro-ethane

4: TMSOTf / acetonitrile / -40 °C

5: NaOMe

6: 86 percent / BF₃*OEt₂, 4A molecular sieves / CH₂Cl₂ / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; hydrazinium monoacetate; caesium carbonate; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja984062p

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

methyl (2,4-diazido-2,4-dideoxy-β-D-xylopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

methyl 2,4-diazido-2,4-dideoxy-β-D-xylopyranoside

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