(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde
• CAS No.: 1400906-90-2
• Molecular Formula: C₃₄H₃₄O₅S
• Molecular Weight: 554.707

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde

Chemical Property:

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde

There total 1 articles about (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde 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: 89.0%

((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol (479252-05-6) → (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde (1400906-90-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1021/acsmedchemlett.1c00349

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde (1400906-90-2) + Methyltriphenylphosphonium bromide (1779-49-3) → p-tolyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1-thio-β-D-glucohept-6-enopyranoside (1400906-91-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -70 - 0 ℃;

DOI:10.1021/jo300986c

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-2-carbaldehyde (1400906-90-2) + methylmagnesium bromide (75-16-1) → p-methylphenyl 2,3,4-tri-O-benzyl-7-deoxy-1-thio-L-glycero-D-glucoheptopyranoside + p-methylphenyl 2,3,4-tri-O-benzyl-7-deoxy-1-thio-D-glycero-D-gluco-heptopyranoside

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.1c01535

upstream raw materials:

((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol

Downstream raw materials:

p-tolyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1-thio-β-D-glucohept-6-enopyranoside

p-tolyl-2,3,4-tri-O-benzyl-8-methyl-1-thio-β-D-glucooctopyrano-7-ulose

1-p-tolyl-2,3,4-tri-O-benzyl-8-deoxy-8-diazo-1-thio-β-D-glucooctopyrano-7-ulose

p-tolyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucoheptopyranoside 7-methanate

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