Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester
• CAS No.: 477329-91-2
• Molecular Formula: C₅₀H₅₅N₁₅O₁₂
• Molecular Weight: 1058.08

Synonyms:Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-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: 32.0%

1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (236115-80-3) + 2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate (477329-89-8) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester (477329-91-2)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃; for 0.666667h;

DOI:10.1021/ol026588r

Reference yield:

2-Azido-1-((3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester (477329-91-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2.57 g / NaBH₄ / methanol / 0 °C

2.1: AcOH; H₂O; TFA / 2 h / 60 °C

2.2: 43 percent / TFA / 20 °C

3.1: hydrazine acetate / dimethylformamide / 20 °C

4.1: DBU / CH₂Cl₂ / 20 °C

5.1: 32 percent / BF₃*OEt₂; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.67 h / -50 °C

With sodium tetrahydroborate; 4 A molecular sieve; boron trifluoride diethyl etherate; water; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol026588r

Reference yield:

6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose (23313-05-5) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-azidomethyl-4-benzyloxy-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]-tetrahydro-pyran-3-yl ester (477329-91-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (COCl)2; DMSO; DIPEA / CH₂Cl₂ / -78 - 0 °C

2.1: 2.57 g / NaBH₄ / methanol / 0 °C

3.1: AcOH; H₂O; TFA / 2 h / 60 °C

3.2: 43 percent / TFA / 20 °C

4.1: hydrazine acetate / dimethylformamide / 20 °C

5.1: DBU / CH₂Cl₂ / 20 °C

6.1: 32 percent / BF₃*OEt₂; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.67 h / -50 °C

With sodium tetrahydroborate; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; water; hydrazinium monoacetate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation;

DOI:10.1021/ol026588r

upstream raw materials:

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

2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose

(R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate

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