[(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol

Base Information

• Chemical Name: [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol
• CAS No.: 350501-48-3
• Molecular Formula: C₄₉H₅₇NO₈
• Molecular Weight: 787.993
• Mol file: 350501-48-3.mol

Synonyms:

Chemical Property of [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol

There total 5 articles about [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-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: 62.0%

(2R,3S,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-pentanedial (350501-47-2) + C-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-methylamine (350501-46-1) → [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol (350501-48-3)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid;

DOI:10.1016/S0040-4039(01)00486-5

Reference yield:

[(2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl]-methanol → [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol (350501-48-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Ac₂O / H₂SO₄

1.2: 71 percent / MeONa / methanol

2.1: NaIO₄ / H₂O; methanol

3.1: 62 percent / NaBH₃CN / acetic acid; methanol

With sodium periodate; acetic anhydride; sodium cyanoborohydride; sulfuric acid; In methanol; water; acetic acid;

DOI:10.1016/S0040-4039(01)00486-5

Reference yield:

Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (191485-91-3) → [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol (350501-48-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 43 percent / toluene

2: 43 percent / LiHBEt₃ / tetrahydrofuran

3: 62 percent / NaBH₃CN / acetic acid; methanol

With lithium triethylborohydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; acetic acid; toluene;

DOI:10.1016/S0040-4039(01)00486-5

upstream raw materials:

(2R,3S,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-pentanedial

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

Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

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