(2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

Base Information

Chemical Name:(2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol
CAS No.:127138-47-0
Molecular Formula:C₃₉H₄₄O₁₀
Molecular Weight:672.772
Hs Code.:

Synonyms:(2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

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Chemical Property of (2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

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Technology Process of (2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

There total 12 articles about (2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol 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: 91.0%

: 127138-45-8
benzyl 4-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 127138-47-0
(2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

Guidance literature:: With sodium methylate; In methanol; for 3h; Ambient temperature;

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-glucose pentaacetate

: 127138-47-0
(2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / HBr / CH₂Cl₂; acetic acid / 3 h / 0 °C

2: 79 percent / HgO (yellow), HgBr₂, drierite / CH₂Cl₂ / 16 h / Ambient temperature

3: 89 percent / 0.02 M NaOCH₃ / methanol / 12 h / Ambient temperature

4: 75 percent / zinc chloride / 48 h

5: 1) KOH / 1.) DMF, cooling 2.) up to r.t., 3 h

6: 90 percent / hydrogen chloride, sodium cyanoborohydride / molecular sieves (3 Angstroem) / diethyl ether; tetrahydrofuran / 0.25 h / Ambient temperature

7: 75 percent / 1) tetramethylurea/silver trifluoromethanesulphonate / CH₂Cl₂ / 1.) -70 deg C 2.) 0 deg C, 4 h 3.) r.t., 10 h

8: 91 percent / CH₃ONa / methanol / 3 h / Ambient temperature

With hydrogenchloride; calcium sulfate; potassium hydroxide; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; tetramethylurea; mercury dibromide; mercury(II) oxide; zinc(II) chloride; 3 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid;

Reference yield:

: 58006-32-9
benzyl 4,6-O-benzylidene-β-D-glucopyranoside

: 127138-47-0
(2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1: 1) KOH / 1.) DMF, cooling 2.) up to r.t., 3 h

2: 90 percent / hydrogen chloride, sodium cyanoborohydride / molecular sieves (3 Angstroem) / diethyl ether; tetrahydrofuran / 0.25 h / Ambient temperature

3: 75 percent / 1) tetramethylurea/silver trifluoromethanesulphonate / CH₂Cl₂ / 1.) -70 deg C 2.) 0 deg C, 4 h 3.) r.t., 10 h

4: 91 percent / CH₃ONa / methanol / 3 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; tetramethylurea; 3 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;