(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one

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Chemical Name:(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one
CAS No.:40246-34-2
Molecular Formula:C₃₉H₄₆O₁₁
Molecular Weight:690.788
Hs Code.:

(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one

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Chemical Property of (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one

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Technology Process of (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one

There total 11 articles about (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one 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: 58.5%

: 40246-33-1
3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

: 40246-34-2
(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one

: 6-O-(3,6-di-O-benzyl-β-D-glycero-hex-3-enopyranos-2-ulosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Guidance literature:: With acetic anhydride; dimethyl sulfoxide; at 20 ℃; for 48h;
DOI:10.3987/COM-03-S60

Reference yield:

: 158852-31-4
3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

: 40246-34-2
(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / 33percent HBr / acetic acid; CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) NaI, 2.) DBU / 1.) acetone, r.t., 15 min, 2.) 45 min

3: 92 percent / NBS, molecular sieves (3 Angstroem) / ethanol; CH₂Cl₂ / 0.03 h / 25 °C

4: Ag₂CO₃, molecular sieves (4 Angstroem) / CH₂Cl₂ / 0.02 h / Ambient temperature

With N-Bromosuccinimide; 3 A molecular sieve; 4 A molecular sieve; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; sodium iodide; In ethanol; dichloromethane; acetic acid;
DOI:10.1021/jo00101a035

Reference yield:

: 38081-38-8
3,4,6-tri-O-acetyl-1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose

: 40246-34-2
(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / KOH / tetrahydrofuran / 3 h / Heating

2: 89 percent / 33percent HBr / acetic acid; CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) NaI, 2.) DBU / 1.) acetone, r.t., 15 min, 2.) 45 min

4: 92 percent / NBS, molecular sieves (3 Angstroem) / ethanol; CH₂Cl₂ / 0.03 h / 25 °C

5: Ag₂CO₃, molecular sieves (4 Angstroem) / CH₂Cl₂ / 0.02 h / Ambient temperature

With potassium hydroxide; N-Bromosuccinimide; 3 A molecular sieve; 4 A molecular sieve; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1021/jo00101a035