Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 102650-46-4
• Molecular Formula: C₂₄H₃₂O₇Si
• Molecular Weight: 460.599
• Mol file: 102650-46-4.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

There total 2 articles about Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-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: 90.0%

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-45-3) → Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-46-4,114027-47-3)

Guidance literature:

With pyridine; chromium(VI) oxide;

DOI:10.1021/jo00363a047

Reference yield:

Benzoic acid (2S,3R,4S,6S)-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-44-2) → Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-46-4,114027-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Pd(OH)2/C / ethyl acetate; methanol

2: 90 percent / CrO₃, pyridine

With pyridine; chromium(VI) oxide; palladium dihydroxide; In methanol; ethyl acetate;

DOI:10.1021/jo00363a047

Reference yield:

Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-46-4,114027-47-3) → (2S,4S,5R,6R)-5-Amino-4-benzoyloxy-2-methoxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 10 steps

1: KHMDS

2: 87 percent / osmium tetraoxide / pyridine

3: lithium triethylborohydride / tetrahydrofuran

4: DMAP / CH₂Cl₂

5: 1.) RuO₂, NaIO₄, NaHCO₃

6: HF / methanol

7: 62 percent / K₂CO₃ / CH₂Cl₂

8: 95 percent / DMAP

9: 50 percent / sodium azide / dimethylformamide

10: Pd(OH)2/C / ethyl acetate; methanol

With dmap; ruthenium(IV) oxide; sodium periodate; osmium(VIII) oxide; sodium azide; hydrogen fluoride; potassium hexamethylsilazane; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00363a047

upstream raw materials:

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4S,6S)-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3S,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((1S,2S)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-((1R,2S)-1,2-dihydroxy-2-methoxycarbonyl-ethyl)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

(2S,4S,5S,6R)-5-Benzoyloxy-4-hydroxy-2-methoxy-6-((1R,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester