((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

Base Information

• Chemical Name: ((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane
• CAS No.: 384819-75-4
• Molecular Formula: C₄₄H₅₁IO₁₀Si
• Molecular Weight: 894.873

Synonyms:

Chemical Property of ((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

There total 6 articles about ((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane 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:

3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (51532-75-3,16697-49-7,68681-00-5,68779-52-2,78418-56-1,125135-29-7,130694-47-2,130694-49-4,146864-77-9) → ((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane (384819-75-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: AcOH / H₂O / 20 °C

1.2: PCC; 4 Angstroem mol. sieves / CH₂Cl₂ / 20 °C

2.1: tetrahydrofuran; pyridine / -40 - 20 °C

3.1: MeONa / methanol / 20 °C

4.1: DMAP / tetrahydrofuran

With dmap; sodium methylate; acetic acid; In tetrahydrofuran; pyridine; methanol; water; 2.1: Tebbe methylenation;

DOI:10.1016/S0040-4039(01)01533-7

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-3-iodo-β-D-allopyranoside (117605-32-0) → ((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane (384819-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran

1.2: tetrahydrofuran

2.1: DMAP / tetrahydrofuran

With dmap; n-butyllithium; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)01533-7

Reference yield:

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71117-37-8) → ((3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-((2R,4aR,6R,7S,8R,8aR)-8-iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane (384819-75-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 68 percent / PPh₃; I₂; imidazole / toluene / 70 °C

2.1: BuLi / tetrahydrofuran

2.2: tetrahydrofuran

3.1: DMAP / tetrahydrofuran

With 1H-imidazole; dmap; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(01)01533-7

upstream raw materials:

2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-1-heptenitol

3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

methyl 4,6-O-benzylidene-3-deoxy-3-iodo-β-D-allopyranoside

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Downstream raw materials:

(2R,4aR,6R,7R,8R,8aS)-8-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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