Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
CAS No.:479623-61-5
Molecular Formula:C₄₁H₄₀O₇
Molecular Weight:644.764
Hs Code.:

Synonyms:Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 4 articles about Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl 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:

: 479623-58-0
3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(benzyl orthobenzoate)

: 479623-61-5
Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With t-butyldimethylsiyl triflate; benzyl alcohol; In dichloromethane; at 20 ℃; for 0.0833333h;
DOI:10.1016/S0040-4020(02)00671-3

Reference yield:

: 14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4
2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

: 479623-61-5
Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine; Bu₄NI / CH₂Cl₂ / 24 h / Heating

2: NaOMe / methanol; tetrahydrofuran

3: imidazole; NaH / dimethylformamide / 2 h / 70 °C

4: BnOH; TBDMSOTf / CH₂Cl₂ / 0.08 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; benzyl alcohol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00671-3

Reference yield:

: 2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3
1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside

: 479623-61-5
Benzoic acid (2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / Ac₂O; 30 percent HBr/AcOH / CH₂Cl₂ / 1 h / 0 °C

2: 2,6-lutidine; Bu₄NI / CH₂Cl₂ / 24 h / Heating

3: NaOMe / methanol; tetrahydrofuran

4: imidazole; NaH / dimethylformamide / 2 h / 70 °C

5: BnOH; TBDMSOTf / CH₂Cl₂ / 0.08 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; hydrogen bromide; sodium methylate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; benzyl alcohol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00671-3