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

Base Information

• 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
• Mol file: 224324-96-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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 → 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 (224324-96-3)

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:

(3aR,4S,6R,6aS)-6-(hydroxymethyl)-2,2-dimethylperhydrocyclopenta[d][1,3]dioxol-4-ol (4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1) → 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 (224324-96-3)

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:

tert-butylchlorodiphenylsilane (58479-61-1) → 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 (224324-96-3)

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

upstream raw materials:

(3aR,4S,6R,6aS)-6-(hydroxymethyl)-2,2-dimethylperhydrocyclopenta[d][1,3]dioxol-4-ol

tert-butylchlorodiphenylsilane

(3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

Downstream raw materials:

3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

(3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine

(R)-1-Benzyloxy-1-{(4R,5R)-5-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-2-one