methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside
CAS No.:175909-98-5
Molecular Formula:C₄₃H₅₁NO₁₁S
Molecular Weight:789.944
Hs Code.:

Synonyms:methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

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Chemical Property of methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

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Technology Process of methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

There total 1 articles about methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-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: 70.0%

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 160584-08-7
1-O-Acetyl-2,3:5,6-di-O-isopropylidene-1-(2-thiazolyl)-α-D-mannofuranose

: 175909-98-5
methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 - 24 ℃; for 1h;
DOI:10.1016/0040-4020(95)01095-5

Reference yield:

: 175909-98-5
methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

: [(3aS,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-methanol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) MeOTf, activated 4 Angstroem molecular sieves, 2.) NaBH₄, 3.) CuO, CuCl₂*2H₂O

2: NaBH₄ / methanol; diethyl ether / 0.17 h / Ambient temperature

With sodium tetrahydroborate; 4 A molecular sieve; methyl trifluoromethanesulfonate; copper(II) oxide; In methanol; diethyl ether;
DOI:10.1016/0040-4020(95)01095-5

Reference yield:

: 175909-98-5
methyl 2,3,4-tri-O-benzyl-6-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

: (3aS,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) MeOTf, activated 4 Angstroem molecular sieves, 2.) NaBH₄, 3.) CuO, CuCl₂*2H₂O

2: KOH, I₂ / diethyl ether

With potassium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; iodine; methyl trifluoromethanesulfonate; copper(II) oxide; In diethyl ether;
DOI:10.1016/0040-4020(95)01095-5