(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran
• CAS No.: 214476-15-0
• Molecular Formula: C₂₉H₃₄O₅
• Molecular Weight: 462.586

Synonyms:(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran

Chemical Property of (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran

There total 4 articles about (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran 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-D-glucal (55628-54-1) → (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran (214476-15-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / NaOH, H₂O, Et₃NBnCl / benzene / 5 h / Ambient temperature

2: 78 percent / Bu₃SnH, AIBN / benzene / Heating

3: NIS / 48 h / Ambient temperature

4: Bu₃SnH, AIBN

With sodium hydroxide; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); N-benzyl-N,N,N-triethylammonium chloride; water; tri-n-butyl-tin hydride; In benzene;

DOI:10.1055/s-1998-3140

Reference yield:

(1S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-7,7-dichloro-2-oxa-bicyclo[4.1.0]heptane (162332-13-0) → (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran (214476-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / Bu₃SnH, AIBN / benzene / Heating

2: NIS / 48 h / Ambient temperature

3: Bu₃SnH, AIBN

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;

DOI:10.1055/s-1998-3140

Reference yield:

(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-iodomethyl-6-methoxy-tetrahydro-pyran → (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran (214476-15-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Yield given;

DOI:10.1055/s-1998-3140

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucal

3,4,6-tri-O-benzyl-1,5-anhydro-2-deoxy-1,2-C-methylene-D-glycero-D-gulohexitol

(1S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-7,7-dichloro-2-oxa-bicyclo[4.1.0]heptane

Downstream raw materials:

(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

(R)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-carbaldehyde

(1S,4S,5R,6R)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-4-hydroxy-5-methyl-10-(tetrahydro-pyran-2-yloxy)-1,6-bis-triethylsilanyloxy-decan-2-one

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