Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol

Base Information

• Chemical Name: Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol
• CAS No.: 219969-04-7
• Molecular Formula: C₅₅H₅₆O₉
• Molecular Weight: 861.044

Synonyms:Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol

Chemical Property of Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol

Chemical Property:

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Technology Process of Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol

There total 7 articles about Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol 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: 86.0%

Bis-((4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-methanol (219969-03-6) → Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol (219969-04-7)

Guidance literature:

With Raney Ni W-2; In tetrahydrofuran; for 0.75h;

DOI:10.1055/s-1998-4503

Reference yield:

1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-2-((S)-phenylsulfinyl)-D-lyxo-hex-1-enitol (125710-64-7) → Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol (219969-04-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, HMPA, -100 deg C, 1.5 h, 2.) THF, HMPA, -100 deg C, 2 h

2: 86 percent / NaCNBH₃, HOAc / 1.) r.t., 10 h, 2.) 50 deg C, 4 h

3: 86 percent / Raney Ni W-2 / tetrahydrofuran / 0.75 h

With Raney Ni W-2; sodium cyanoborohydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1055/s-1998-4503

Reference yield:

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-(R)-phenylsulfinyl-D-lyxo-hex-1-enitol → Bis-((4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methanol (219969-04-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, HMPA, -100 deg C, 1.5 h, 2.) THF, HMPA, -100 deg C, 2 h

2: 86 percent / NaCNBH₃, HOAc / 1.) r.t., 10 h, 2.) 50 deg C, 4 h

3: 86 percent / Raney Ni W-2 / tetrahydrofuran / 0.75 h

With Raney Ni W-2; sodium cyanoborohydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1055/s-1998-4503

upstream raw materials:

Bis-((4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-methanol

1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-2-((S)-phenylsulfinyl)-D-lyxo-hex-1-enitol

2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-3-(S)-phenylsulfinyl-aldehydo-D-lyxo-hept-2-enose

2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-3-(R)-phenylsulfinyl-aldehydo-D-lyxo-hept-2-enose

Downstream raw materials:

bis(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)methyl 4-methoxybenzyl ether

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