Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester
CAS No.:316792-05-9
Molecular Formula:C₂₂H₂₇NO₉S
Molecular Weight:481.524
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester 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:

: 1772-03-8,4710-95-6,6730-09-2,14131-59-0,14131-62-5,14131-63-6,14131-65-8,14131-67-0,14257-79-5,19124-46-0,20706-90-5,91673-92-6
D-(+)-galactosamine hydrochloride

: 316792-05-9
Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: IRA-400 resin / H₂O

1.2: DIPEA / methanol / 14 h / 20 °C

2.1: BF₃*OEt₂ / 16 h / 70 °C

3.1: pyridine / 5 h / 20 °C

With pyridine; IRA-400 resin; boron trifluoride diethyl etherate; In water; 1.1: Neutralization / 1.2: Acylation / 2.1: Etherification / 3.1: Tosylation;
DOI:10.1002/1521-3773(20001016)39:20<3656::AID-ANIE3656>3.0.CO;2-O

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 316792-04-8
((3R,4R,5R,6R)-2-Benzyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid methyl ester

: 316792-05-9
Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With pyridine; at 20 ℃; for 5h;
DOI:10.1002/1521-3773(20001016)39:20<3656::AID-ANIE3656>3.0.CO;2-O

Reference yield:

: ((3R,4R,5R,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid methyl ester

: 316792-05-9
Toluene-4-sulfonic acid (2R,3R,4R,5R)-6-benzyloxy-3,4-dihydroxy-5-methoxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: BF₃*OEt₂ / 16 h / 70 °C

2: pyridine / 5 h / 20 °C

With pyridine; boron trifluoride diethyl etherate; 1: Etherification / 2: Tosylation;
DOI:10.1002/1521-3773(20001016)39:20<3656::AID-ANIE3656>3.0.CO;2-O