2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine

Base Information

• Chemical Name: 2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine
• CAS No.: 181506-87-6
• Molecular Formula: C₃₈H₄₇NO₇SSi
• Molecular Weight: 689.945

Synonyms:2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine

Chemical Property of 2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine

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Technology Process of 2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine

There total 1 articles about 2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine 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: 78.0%

t-butyldimethylsiyl triflate (69739-34-0) + 3,4,6-tri-O-benzyl-α-D-mannopyranosyl 2-pyridyl sulfone (168985-18-0) → 2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine (181506-87-6)

Guidance literature:

With dmap; TEA; In dichloromethane; at 0 ℃;

DOI:10.1039/CC9960001661

Reference yield: 85.0%

2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine (181506-87-6) + p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-formyl-α-D-mannopyranoside (188893-05-2) → p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside (188893-20-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(97)00206-2

Reference yield: 80.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + 2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine (181506-87-6) → 1-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-cyclohexanol

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(97)00206-2

upstream raw materials:

t-butyldimethylsiyl triflate

3,4,6-tri-O-benzyl-α-D-mannopyranosyl 2-pyridyl sulfone

Downstream raw materials:

Methyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

(R)-1-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-nonan-1-ol

(S)-1-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-nonan-1-ol

p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

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