(2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol
• CAS No.: 85207-05-2
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472

Synonyms:(2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol

Chemical Property of (2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol

Chemical Property:

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Technology Process of (2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol

There total 4 articles about (2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol 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: 71.0%

(4aR,6S,7R,8S,8aS)-6-Allyloxy-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (85207-04-1) → (2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol (85207-05-2)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride;

DOI:10.1016/0008-6215(82)84021-4

Reference yield:

1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside (65987-12-4) → (2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol (85207-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent

2: 71 percent / LiAlH₄, AlCl₃

With lithium aluminium tetrahydride; aluminium trichloride;

DOI:10.1016/0008-6215(82)84021-4

Reference yield:

benzaldehyde (100-52-7) → (2S,3R,4S,5S,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-ol (85207-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / ZnCl₂

2: 74 percent

3: 71 percent / LiAlH₄, AlCl₃

With lithium aluminium tetrahydride; aluminium trichloride; zinc(II) chloride;

DOI:10.1016/0008-6215(82)84021-4

upstream raw materials:

(4aR,6S,7R,8S,8aS)-6-Allyloxy-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside

benzaldehyde

1-O-allyl-α-D-glucopyranoside

Downstream raw materials:

Acetic acid (2R,3R,4S,5R,6S)-6-allyloxy-3,5-bis-benzyloxy-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Acetic acid (2R,3R,4S,5R,6S)-6-allyloxy-3,5-bis-benzyloxy-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Acetic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-hydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-6-chloro-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

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