benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside

Base Information

Chemical Name:benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside
CAS No.:175910-15-3
Molecular Formula:C₂₂H₂₇NO₆S
Molecular Weight:433.525
Hs Code.:

Synonyms:benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside

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Technology Process of benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside

There total 1 articles about benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside 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: 97.0%

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

: 100-51-6,185532-71-2
benzyl alcohol

: 175910-15-3
benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1016/0040-4020(95)01095-5

Reference yield:

: 175910-15-3
benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside

: (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 5 steps

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

2: KOH, I₂ / diethyl ether

3: H₂ / 10percent Pd/C / ethyl acetate / Ambient temperature

4: Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

5: 5 percent / trimethylsilyl triflate, activated 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 - 24 °C

With potassium hydroxide; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; iodine; triethylamine; methyl trifluoromethanesulfonate; copper(II) oxide; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1016/0040-4020(95)01095-5

Reference yield:

: 175910-15-3
benzyl 2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranoside

: 175910-16-4
methyl (benzyl 3,4:6,7-di-O-isopropylidene-α-D-manno-heptulofuranosid)onate

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