ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 495391-13-4
• Molecular Formula: C₂₉H₃₇NO₆SSi
• Molecular Weight: 555.767

Synonyms:ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 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: 97.0%

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) + tert-butyldimethylsilyl chloride (18162-48-6) → ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (495391-13-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 90 ℃; for 3h;

DOI:10.1016/j.carres.2019.107824

Reference yield: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (495391-13-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane;

DOI:10.1016/S0040-4039(02)01753-7

Reference yield: 82.0%

ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (495391-13-4) → ethyl 4-O-benzyl-2-deoxy-2-phthalimido-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; diborane; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 5h; regioselective reaction;

DOI:10.1016/j.carres.2019.107824

upstream raw materials:

t-butyldimethylsiyl triflate

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₅₉H₆₅N₅O₁₄Si

N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(3-azido-propoxy)-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

N-[6-[5-acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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