3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

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Chemical Name:3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
CAS No.:224324-96-3
Molecular Formula:C₆₀H₆₈O₉Si
Molecular Weight:961.28
Hs Code.:

Synonyms:3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

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Chemical Property of 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

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Technology Process of 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

There total 7 articles about 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 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: 88.0%

: tert-Butyl-{(R)-2-((4S,5R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-2-[1-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-vinyloxy]-ethoxy}-diphenyl-silane

: 224324-96-3
3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1021/jo991898h

Reference yield:

: 4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1
(3aR,4S,6R,6aS)-6-(hydroxymethyl)-2,2-dimethylperhydrocyclopenta[d][1,3]dioxol-4-ol

: 224324-96-3
3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 95 percent / imidazole / dimethylformamide / 1.5 h / 50 °C

2.1: 95 percent / I₂ / cyclohexane / 3 h / 20 °C

3.1: BF₃*Et₂O / CH₂Cl₂ / 1 h / -40 °C

3.2: 90 percent / NH₃ / methanol / 0.5 h / 20 °C

4.1: 97.2 percent / DCC; DMAP / benzene / 1.5 h / 0 - 20 °C

5.1: 88 percent / pyridine / toluene; tetrahydrofuran / 1 h / -78 °C

6.1: 88 percent / methyl triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 20 °C

With pyridine; 1H-imidazole; dmap; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; iodine; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; benzene; 1.1: silylation / 2.1: Ring cleavage / 3.1: Substitution / 3.2: deesterification / 4.1: Esterification / 5.1: methylenation / 6.1: Cyclization;
DOI:10.1021/jo991898h

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 224324-96-3
3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 95 percent / imidazole / dimethylformamide / 1.5 h / 50 °C

2.1: 95 percent / I₂ / cyclohexane / 3 h / 20 °C

3.1: BF₃*Et₂O / CH₂Cl₂ / 1 h / -40 °C

3.2: 90 percent / NH₃ / methanol / 0.5 h / 20 °C

4.1: 97.2 percent / DCC; DMAP / benzene / 1.5 h / 0 - 20 °C

5.1: 88 percent / pyridine / toluene; tetrahydrofuran / 1 h / -78 °C

6.1: 88 percent / methyl triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 20 °C

With pyridine; 1H-imidazole; dmap; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; iodine; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; benzene; 1.1: silylation / 2.1: Ring cleavage / 3.1: Substitution / 3.2: deesterification / 4.1: Esterification / 5.1: methylenation / 6.1: Cyclization;
DOI:10.1021/jo991898h