Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester

Base Information

• Chemical Name: Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester
• CAS No.: 228106-23-8
• Molecular Formula: C₂₉H₄₁N₃O₈Si
• Molecular Weight: 587.745

Synonyms:Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester

Chemical Property of Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester

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Technology Process of Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester

There total 4 articles about Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl 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: 74.0%

Acetic acid 4-[(2R,4aR,6S,7R,8R,8aS)-7-azido-6-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-2-yl]-phenyl ester (228106-34-1) → Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester (228106-23-8)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 20 ℃;

DOI:10.1021/ja9836085

Reference yield:

4-formylphenyl acetate (878-00-2) → Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester (228106-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / ZnCl₂ / CH₂Cl₂ / 18 h / 20 °C

2: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / -78 °C

3: 74 percent / HCl, NaBH₃CN / diethyl ether; tetrahydrofuran / 20 °C

With hydrogenchloride; boron trifluoride diethyl etherate; sodium cyanoborohydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja9836085

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-67-9) → Acetic acid 4-[(2R,3S,4R,5R,6S)-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl ester (228106-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / ZnCl₂ / CH₂Cl₂ / 18 h / 20 °C

2: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / -78 °C

3: 74 percent / HCl, NaBH₃CN / diethyl ether; tetrahydrofuran / 20 °C

With hydrogenchloride; boron trifluoride diethyl etherate; sodium cyanoborohydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja9836085

upstream raw materials:

Acetic acid 4-[(2R,4aR,6S,7R,8R,8aS)-7-azido-6-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-2-yl]-phenyl ester

4-formylphenyl acetate

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

Acetic acid 4-[(2R,4aR,6S,7R,8R,8aS)-7-azido-6-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-hexahydro-pyrano[3,2-d][1,3]dioxin-2-yl]-phenyl ester

Downstream raw materials:

C₆₃H₆₇N₃O₁₇Si

C₅₅H₅₉N₃O₁₆Si

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