ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside
CAS No.:843674-49-7
Molecular Formula:C₃₂H₄₃ClO₁₀S
Molecular Weight:655.206
Hs Code.:

Synonyms:ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

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Technology Process of ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

There total 7 articles about ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside 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: 80.0%

: 843674-48-6
ethyl (2'S,3'S)-7-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

: 79-04-9
chloroacetyl chloride

: 843674-49-7
ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 0.75h;
DOI:10.1081/CAR-200044580

Reference yield:

: (2S,3S,4aS,5S,7R,8S,8aS)-7-Ethylsulfanyl-2,3-dimethoxy-8-(4-methoxy-benzyloxy)-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxine-5-carbaldehyde

: 843674-49-7
ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: tetrahydrofuran / 0 - 30 °C

2: 80 percent / pyridine / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; In tetrahydrofuran; dichloromethane; 1: Barbier reaction;
DOI:10.1081/CAR-200044580

Reference yield:

: 843674-47-5
ethyl (2'S,3'S)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

: 843674-49-7
ethyl (2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl chloride; DMSO; N,N-diisopropylethylamine / tetrahydrofuran / -70 - 20 °C

2: tetrahydrofuran / 0 - 30 °C

3: 80 percent / pyridine / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation / 2: Barbier reaction;
DOI:10.1081/CAR-200044580