(2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol

Base Information

• Chemical Name: (2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol
• CAS No.: 219697-69-5
• Molecular Formula: C₁₇H₂₆O₅SSi
• Molecular Weight: 370.542
• Mol file: 219697-69-5.mol

Synonyms:(2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol

Chemical Property of (2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol

There total 1 articles about (2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol 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: 71.0%

phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribofuranosyl sulfone → (2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol (219697-69-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; a) -78 deg C, 1 h, b) RT, 2 h;

DOI:10.1139/v98-112

Reference yield: 89.0%

benzyl isothiocyanate (3173-56-6) + (2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol (219697-69-5) → phenyl 2-benzylamino-5-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-ribofuranosyl sulfone

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; a) 0 deg C, 1 h, b) RT, 20 h;

DOI:10.1139/v98-112

Reference yield:

(2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol (219697-69-5) → (4S,5R)-3-benzyl-4-(benzyloxymethyl)-5-vinyl-2-oxazolidinone (219697-74-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / t-BuOK / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 20 h

2: 88 percent / Me₃SiCl, MeOH / 1 h / 0 °C

3: 95 percent / I₂, Ph₃P, pyridine / toluene; CH₂Cl₂ / 4 h / Heating

4: Zn/Ag / tetrahydrofuran / 1 h / 60 °C

5: NaBH₄ / tetrahydrofuran; aq. ethanol / a) 0 deg C, 2 h, b) RT, overnight

6: 86 percent / NaH / tetrahydrofuran / 20 h / 0 - 20 °C

With pyridine; methanol; sodium tetrahydroborate; chloro-trimethyl-silane; potassium tert-butylate; iodine; silver; sodium hydride; triphenylphosphine; zinc; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1139/v98-112

Downstream raw materials:

(4S,5R)-3-benzyl-4-(benzyloxymethyl)-5-vinyl-2-oxazolidinone

(4S,5R)-3-benzyl-4-(hydroxymethyl)-5-vinyl-2-oxazolidinone

phenyl 2-benzylamino-2N,3O-carbamoyl-2-deoxy-α-D-ribofuranosyl sulfone

phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone