C₆H₇O(OCOCH₃)4OCH₂CH₂NHCO₂OCHN₃CHOCH₂C₆H₅CHOCH₂C₆H₅CHOCH₂C₆H₄OCH₃CHCH₂CONCH₂CH₂O₂C₆H₇(OCOCH₃)4

Base Information

• Chemical Name: C₆H₇O(OCOCH₃)4OCH₂CH₂NHCO₂OCHN₃CHOCH₂C₆H₅CHOCH₂C₆H₅CHOCH₂C₆H₄OCH₃CHCH₂CONCH₂CH₂O₂C₆H₇(OCOCH₃)4
• CAS No.: 288844-60-0
• Molecular Formula: C₆₂H₇₇N₅O₂₈
• Molecular Weight: 1340.31

Synonyms:C₆H₇O(OCOCH₃)4OCH₂CH₂NHCO₂OCHN₃CHOCH₂C₆H₅CHOCH₂C₆H₅CHOCH₂C₆H₄OCH₃CHCH₂CONCH₂CH₂O₂C₆H₇(OCOCH₃)4

Chemical Property of C₆H₇O(OCOCH₃)4OCH₂CH₂NHCO₂OCHN₃CHOCH₂C₆H₅CHOCH₂C₆H₅CHOCH₂C₆H₄OCH₃CHCH₂CONCH₂CH₂O₂C₆H₇(OCOCH₃)4

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Technology Process of C₆H₇O(OCOCH₃)4OCH₂CH₂NHCO₂OCHN₃CHOCH₂C₆H₅CHOCH₂C₆H₅CHOCH₂C₆H₄OCH₃CHCH₂CONCH₂CH₂O₂C₆H₇(OCOCH₃)4

There total 4 articles about C₆H₇O(OCOCH₃)4OCH₂CH₂NHCO₂OCHN₃CHOCH₂C₆H₅CHOCH₂C₆H₅CHOCH₂C₆H₄OCH₃CHCH₂CONCH₂CH₂O₂C₆H₇(OCOCH₃)4 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: 94.0%

2-(p-nitrophenylcarbamate)-ethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (272128-75-3) + 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyl azide (288844-57-5) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{2-[(2R,3R,4S,5R,6R)-6-azido-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxycarbonylamino]-ethoxy}-tetrahydro-pyran-3-yl ester + C6H7O(OCOCH3)4OCH2CH2NHCO2OCHN3CHOCH2C6H5CHOCH2C6H5CHOCH2C6H4OCH3CHCH2CONCH2CH2O2C6H7(OCOCH3)4 (288844-60-0)

Guidance literature:

With sodium hydride; triethylamine; In tetrahydrofuran; at 60 ℃; for 6h;

DOI:10.1021/ol0060127

Reference yield:

4,6-O-p-methoxybenzylidene-β-D-glucopyranosyl azide → C6H7O(OCOCH3)4OCH2CH2NHCO2OCHN3CHOCH2C6H5CHOCH2C6H5CHOCH2C6H4OCH3CHCH2CONCH2CH2O2C6H7(OCOCH3)4 (288844-60-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / NaH / dimethylformamide / 20 °C

2: 93 percent / NaBH₃CN; TMSCl / acetonitrile / 24 h / 20 °C

3: 94 percent / Et₃N; NaH / tetrahydrofuran / 6 h / 60 °C

With chloro-trimethyl-silane; sodium hydride; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: Ring cleavage / 3: transcarbamoylation;

DOI:10.1021/ol0060127

Reference yield:

2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranosyl azide → C6H7O(OCOCH3)4OCH2CH2NHCO2OCHN3CHOCH2C6H5CHOCH2C6H5CHOCH2C6H4OCH3CHCH2CONCH2CH2O2C6H7(OCOCH3)4 (288844-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NaBH₃CN; TMSCl / acetonitrile / 24 h / 20 °C

2: 94 percent / Et₃N; NaH / tetrahydrofuran / 6 h / 60 °C

With chloro-trimethyl-silane; sodium hydride; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; acetonitrile; 1: Ring cleavage / 2: transcarbamoylation;

DOI:10.1021/ol0060127

upstream raw materials:

2-(p-nitrophenylcarbamate)-ethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyl azide

benzyl bromide

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