methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside

Base Information

Chemical Name:methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside
CAS No.:440359-31-9
Molecular Formula:C₂₀H₃₄O₈SSi
Molecular Weight:462.637
Hs Code.:

Synonyms:methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside

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Chemical Property of methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside

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Technology Process of methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside

There total 9 articles about methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 440359-30-8
Toluene-4-sulfonic acid (2R,3S,4S,5S)-3,4-dihydroxy-2-hydroxymethyl-5-methoxy-tetrahydro-furan-3-ylmethyl ester

: 440359-31-9
methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 3h;
DOI:10.1021/jo011127p

Reference yield:

: 26532-10-5
methyl 2,3-anhydro-α-D-lyxofuranoside

: 440359-31-9
methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 83 percent / phenylmethanol / 3 h / 120 °C

2: 74 percent / pyridine / CH₂Cl₂ / 4 h / -78 - 0 °C

3: 94 percent / H₂ / Pd(OH)2 / methanol / 72 h / 20 °C

4: pyridinium chlorochromate; sodium acetate; molecular sieves 4 Angstroem / CH₂Cl₂ / 8 h / 20 °C

5: 273 mg / tetrahydrofuran / 13 h / 70 °C

6: RuCl₃*H₂O; sodium periodate / ethyl acetate; acetonitrile; H₂O / 0.5 h / 0 °C

7: 264 mg / 1,4-diazabicyclo[2.2.2]octane / CH₂Cl₂ / 2 h / 0 °C

8: 85 percent / HF / tetrahydrofuran; pyridine / 4 h / 20 °C

9: 86 percent / imidazole / dimethylformamide / 3 h / 0 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; ruthenium trichloride; sodium periodate; 4 A molecular sieve; hydrogen fluoride; hydrogen; sodium acetate; pyridinium chlorochromate; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzyl alcohol;
DOI:10.1021/jo011127p

Reference yield:

: 440359-25-1
methyl 3-O-benzyl-α-D-arabinofuranoside

: 440359-31-9
methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 74 percent / pyridine / CH₂Cl₂ / 4 h / -78 - 0 °C

2: 94 percent / H₂ / Pd(OH)2 / methanol / 72 h / 20 °C

3: pyridinium chlorochromate; sodium acetate; molecular sieves 4 Angstroem / CH₂Cl₂ / 8 h / 20 °C

4: 273 mg / tetrahydrofuran / 13 h / 70 °C

5: RuCl₃*H₂O; sodium periodate / ethyl acetate; acetonitrile; H₂O / 0.5 h / 0 °C

6: 264 mg / 1,4-diazabicyclo[2.2.2]octane / CH₂Cl₂ / 2 h / 0 °C

7: 85 percent / HF / tetrahydrofuran; pyridine / 4 h / 20 °C

8: 86 percent / imidazole / dimethylformamide / 3 h / 0 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; ruthenium trichloride; sodium periodate; 4 A molecular sieve; hydrogen fluoride; hydrogen; sodium acetate; pyridinium chlorochromate; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo011127p