(2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:(2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside
CAS No.:791836-35-6
Molecular Formula:C₂₂H₃₂O₆S
Molecular Weight:424.558
Hs Code.:

Synonyms:(2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

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Chemical Property of (2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

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Technology Process of (2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

There total 5 articles about (2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside 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: 83.0%

: 791836-34-5
(2'S,3'S)-para-tolyl 3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

: 106-95-6
allyl bromide

: 791836-35-6
(2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.1016/j.tet.2004.07.083

Reference yield:

: 73-34-7
L-rhamnose

: 791836-35-6
(2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / I₂ / 20 °C

2: BF₃*OEt₂ / CH₂Cl₂ / 3 h / 20 °C

3: 97 percent / NaOMe / methanol / 100 h / 20 °C

4: 74 percent / CSA / methanol / 16 h / 75 °C

5: 83 percent / NaH / dimethylformamide; various solvent(s) / 2 h / 0 °C

With camphor-10-sulfonic acid; boron trifluoride diethyl etherate; iodine; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 3: Zemplen deacetylation;
DOI:10.1016/j.tet.2004.07.083

Reference yield:

: 7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4
1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

: 791836-35-6
(2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 3 h / 20 °C

2: 97 percent / NaOMe / methanol / 100 h / 20 °C

3: 74 percent / CSA / methanol / 16 h / 75 °C

4: 83 percent / NaH / dimethylformamide; various solvent(s) / 2 h / 0 °C

With camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 2: Zemplen deacetylation;
DOI:10.1016/j.tet.2004.07.083