methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside
CAS No.:122622-40-6
Molecular Formula:C₂₅H₃₉ClO₅Si
Molecular Weight:483.12
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside

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Technology Process of methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside

There total 4 articles about methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside 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: 69.0%

: 122592-17-0
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2-deoxy-2-C-methyl-3-C-vinyl-α-D-allopyranoside

: 122622-40-6
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside

Guidance literature:: With pyridine; thionyl chloride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/jo00283a034

Reference yield:

: 122622-39-3
(2R,4aR,6S,7R,8S,8aR)-7-(2-Hydroxy-ethyl)-6-methoxy-7-methyl-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 122622-40-6
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

2: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

With pyridine; 1H-imidazole; thionyl chloride; In tetrahydrofuran;
DOI:10.1021/jo00283a034

Reference yield:

: 122672-65-5
methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose

: 122622-40-6
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-3-C-((Z)-2-chloroethylidene)-2,3-dideoxy-2-C-methyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / KH / tetrahydrofuran / 3 h / 0 °C

2: 2.) LiAlH₄ / 1.) THF, 15 min, 2.) THF, 0 deg C, 45 min

3: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

4: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; potassium hydride; In tetrahydrofuran;
DOI:10.1021/jo00283a034