methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside

Base Information

• Chemical Name: methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside
• CAS No.: 91312-66-2
• Molecular Formula: C₂₀H₃₄O₆SSi
• Molecular Weight: 430.638

Synonyms:methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside

Chemical Property of methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside

Chemical Property:

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Technology Process of methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside

There total 1 articles about methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside 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: 90.0%

methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-hydroxy-α-D-erythro-hexopyranoside (91312-63-9) + p-toluenesulfonyl chloride (98-59-9) → methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside (91312-66-2)

Guidance literature:

With pyridine; for 24h; Ambient temperature;

DOI:10.1021/jo00195a023

Reference yield: 88.0%

methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside (91312-66-2) → methyl 2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside (91312-71-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1021/jo00195a023

Reference yield: 55.0%

sodium benzenesulfonate (873-55-2) + methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside (91312-66-2) → methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-iodo-α-D-erythro-hexopyranoside (91312-67-3) + methyl 3-O-(tert-butyldimethylsilyl)-2,4,6-trideoxy-6-(phenylsulfonyl)-α-D-erythro-hexopyranoside (91312-74-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 8h; Heating;

DOI:10.1021/jo00195a023

upstream raw materials:

methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-hydroxy-α-D-erythro-hexopyranoside

p-toluenesulfonyl chloride

Downstream raw materials:

methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-iodo-α-D-erythro-hexopyranoside

methyl 3-O-(tert-butyldimethylsilyl)-2,4,6-trideoxy-6-(phenylsulfonyl)-α-D-erythro-hexopyranoside

methyl 2,4-dideoxy-6-O-(p-tolylsulfonyl)-α-D-erythro-hexopyranoside

((2R,4R,6R)-2-Benzenesulfonylmethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-tert-butyl-dimethyl-silane

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