Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 502621-22-9
• Molecular Formula: C₄₇H₅₆N₁₂O₁₄
• Molecular Weight: 1013.03

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-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: 80.0%

1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (236115-80-3) + 4-O-(2-acetoxyethyl)-2,3-di-O-acetyl-6-deoxy-α-D-glucopyranosyl trichloroacetimidate (502621-08-1) → Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester (502621-22-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃;

DOI:10.1021/ol027288c

Reference yield:

methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside (56750-58-4) → Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester (502621-22-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / NaH; TBAI / tetrahydrofuran; various solvent(s) / 24 h

2.1: O₃ / CH₂Cl₂

2.2: 70 percent / NaBH₄ / methanol; CH₂Cl₂ / 3 h / 0 °C

3.1: 69 percent / H₂SO₄ / 0 °C

4.1: hydrazine acetate / dimethylformamide / 20 °C

5.1: DBU / CH₂Cl₂ / 20 °C

6.1: 80 percent / BF₃*Et₂O / CH₂Cl₂ / -50 °C

With sulfuric acid; boron trifluoride diethyl etherate; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol027288c

Reference yield:

Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-(2-acetoxy-ethoxy)-2-hydroxy-6-methyl-tetrahydro-pyran-4-yl ester → Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-(2-acetoxy-ethoxy)-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester (502621-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / CH₂Cl₂ / 20 °C

2: 80 percent / BF₃*Et₂O / CH₂Cl₂ / -50 °C

With boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1021/ol027288c

upstream raw materials:

1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

4-O-(2-acetoxyethyl)-2,3-di-O-acetyl-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

methyl 4-O-allyl-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside

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