4-O-tosyl-D-arabinal

Base Information

• Chemical Name: 4-O-tosyl-D-arabinal
• CAS No.: 160247-15-4
• Molecular Formula: C₁₂H₁₄O₅S
• Molecular Weight: 270.306
• Mol file: 160247-15-4.mol

Synonyms:

Chemical Property of 4-O-tosyl-D-arabinal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-tosyl-D-arabinal

There total 1 articles about 4-O-tosyl-D-arabinal 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:

p-toluenesulfonyl chloride (98-59-9) + 1,5-anhydro-2-deoxy-D-erythro-pent-1-enitol (496-61-7) → 4-O-tosyl-D-arabinal (160247-15-4)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; Yield given. Multistep reaction; 1) toluene, reflux, 2) toluene, 70 deg C, 30 min;

DOI:10.1039/C39940002127

Reference yield:

4-O-tosyl-D-arabinal (160247-15-4) → C40H53F3N2O12S

Guidance literature:

Multi-step reaction with 10 steps

1: 74 percent / NaN₃ / hexamethylphosphoric acid triamide / 60 °C

2: NaH / tetrahydrofuran / 0 °C

3: PPh₃ / tetrahydrofuran; H₂O / 24 h / Ambient temperature

4: NaBH₃CN, pH 3 / propan-2-ol / Ambient temperature

5: NEt₃ / Ambient temperature

6: 74 percent / N-iodosuccinimide, molecular sieves 4 Angstroem / acetonitrile / -30 - 0 °C

7: 87 percent / Bu₃SnH / toluene / 70 °C

8: 74 percent / NaBH₃CN, BF₃*Et₂O / CH₂Cl₂; tetrahydrofuran / -20 °C

9: 1) 0.3 M aq. HCl / 1) MeOH, r.t., 2) toluene, reflux, 1 h

10: 90 percent / AgOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 0 °C

With hydrogenchloride; N-iodo-succinimide; sodium azide; 4 A molecular sieve; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1039/C39940002127

Reference yield:

4-O-tosyl-D-arabinal (160247-15-4) → C40H53F3N2O12S

Guidance literature:

Multi-step reaction with 10 steps

1: 74 percent / NaN₃ / hexamethylphosphoric acid triamide / 60 °C

2: NaH / tetrahydrofuran / 0 °C

3: PPh₃ / tetrahydrofuran; H₂O / 24 h / Ambient temperature

4: NaBH₃CN, pH 3 / propan-2-ol / Ambient temperature

5: NEt₃ / Ambient temperature

6: 74 percent / N-iodosuccinimide, molecular sieves 4 Angstroem / acetonitrile / -30 - 0 °C

7: 87 percent / Bu₃SnH / toluene / 70 °C

8: 74 percent / NaBH₃CN, BF₃*Et₂O / CH₂Cl₂; tetrahydrofuran / -20 °C

9: 1) 0.3 M aq. HCl / 1) MeOH, r.t., 2) toluene, reflux, 1 h

10: AgOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 0 °C

With hydrogenchloride; N-iodo-succinimide; sodium azide; 4 A molecular sieve; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1039/C39940002127

upstream raw materials:

p-toluenesulfonyl chloride

1,5-anhydro-2-deoxy-D-erythro-pent-1-enitol

Downstream raw materials:

(3S,4S)-4-Methoxy-3,4-dihydro-2H-pyran-3-ylamine

C₂₆H₃₇F₃N₂O₉