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

Base Information

• Chemical Name: 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
• CAS No.: 190970-14-0
• Molecular Formula: C₄₂H₅₆O₁₆Si
• Molecular Weight: 844.983

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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:

1,3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranoside (30253-76-0) → 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 (190970-14-0)

Guidance literature:

Multi-step reaction with 6 steps

1: TMSOTf

2: 95 percent / NIS, TfOH / CH₂Cl₂; diethyl ether / 0.08 h

3: H₂ / Pd/C

5: HOAc, ethylene glycol / H₂O / Heating

6: pyridine

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; hydrogen; ethylene glycol; acetic acid; palladium on activated charcoal; In diethyl ether; dichloromethane; water;

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

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 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 (190970-14-0)

Guidance literature:

Multi-step reaction with 7 steps

2: NaBH₄ / ethanol

3: 95 percent / NIS, TfOH / CH₂Cl₂; diethyl ether / 0.08 h

4: H₂ / Pd/C

6: HOAc, ethylene glycol / H₂O / Heating

7: pyridine

With pyridine; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; ethylene glycol; acetic acid; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; water;

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

Reference yield:

1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose (114861-14-2) → 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 (190970-14-0)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / ethanol

2: 95 percent / NIS, TfOH / CH₂Cl₂; diethyl ether / 0.08 h

3: H₂ / Pd/C

5: HOAc, ethylene glycol / H₂O / Heating

6: pyridine

With pyridine; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; ethylene glycol; acetic acid; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; water;

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

upstream raw materials:

acetic anhydride

1,3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranoside

1,2-O-isopropylidene-α-D-xylose

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

Downstream raw materials:

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

C₇₀H₇₁N₅O₁₅

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