Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester
• CAS No.: 190970-11-7
• Molecular Formula: C₃₆H₄₈O₁₃Si
• Molecular Weight: 716.855

Synonyms:Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester

There total 8 articles about Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-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:

Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-4-yl ester (177412-79-2) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester (190970-11-7)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/0040-4039(96)00632-6

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester (190970-11-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / pyridine / 3 h

2: DMSO, Ac₂O / 16 h

3: NaBH₄ / methanol; CH₂Cl₂

4: 95 percent / NIS, TfOH / 1,2-dichloro-ethane; diethyl ether / 0.08 h

5: H₂, AcOH / Pd/C / propan-2-ol / 16 h / 1810.02 Torr

With pyridine; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; acetic anhydride; acetic acid; dimethyl sulfoxide; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; isopropyl alcohol;

DOI:10.1016/S0040-4020(97)00307-4

Reference yield:

1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose (190970-10-6) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester (190970-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NIS, TfOH / 1,2-dichloro-ethane; diethyl ether / 0.08 h

2: H₂, AcOH / Pd/C / propan-2-ol / 16 h / 1810.02 Torr

With N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; acetic acid; palladium on activated charcoal; In diethyl ether; 1,2-dichloro-ethane; isopropyl alcohol;

DOI:10.1016/S0040-4020(97)00307-4

upstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-4-yl ester

1,2-O-isopropylidene-α-D-xylose

1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose

1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-3-yl ester

C₇₀H₇₁N₅O₁₅

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-3-yl ester

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