(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

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Chemical Name:(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol
CAS No.:615564-35-7
Molecular Formula:C₅₃H₅₆O₁₀
Molecular Weight:853.022
Hs Code.:

Synonyms:(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

There total 3 articles about (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol 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: 65.0%

: ethyl 3,4-di-O-benzyl-1-thio-β-D-xylopyranoside

: 615564-30-2
3,4-dimethoxybenzyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

: 615564-35-7
(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Guidance literature:: ethyl 3,4-di-O-benzyl-1-thio-β-D-xylopyranoside; 3,4-dimethoxybenzyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 4h;

With 2,6-di-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 40 ℃; for 16h;
DOI:10.1021/ol034836t

Reference yield:

: 80300-30-7
1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 615564-35-7
(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: TMSI / CH₂Cl₂ / 1 h / 0 °C

1.2: 80 percent / Bu₄NI; DIEA / CH₂Cl₂ / 16 h / Heating

2.1: DDQ / CH₂Cl₂ / 4 h / 20 °C

2.2: 65 percent / DTBMP; MeOTf / 1,2-dichloro-ethane / 16 h / 40 °C

With trimethylsilyl iodide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1021/ol034836t

Reference yield:

: 115220-82-1
(3R,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran

: 615564-35-7
(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: dimethyl dioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

1.2: 48 percent / trifluoroacetic anhydride / CH₂Cl₂ / 16 h / 0 - 20 °C

2.1: DDQ / CH₂Cl₂ / 4 h / 20 °C

2.2: 65 percent / DTBMP; MeOTf / 1,2-dichloro-ethane / 16 h / 40 °C

With 3,3-dimethyldioxirane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; acetone;
DOI:10.1021/ol034836t