Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester
• CAS No.: 138552-44-0
• Molecular Formula: C₃₇H₄₆O₁₀
• Molecular Weight: 650.766

Synonyms:Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester

Chemical Property of Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester

There total 9 articles about Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester 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:

1,2,3-tri-O-acetyl-4-O-methyl-α-L-rhamnopyranose (72397-96-7) → Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester (138552-44-0)

Guidance literature:

Multi-step reaction with 5 steps

1: HBr / acetic acid

2: 60 percent / Hg(CN)2, HgBr₂

3: deacetylation under Zemplen conditions

4: benzylation

5: deallylation, acetylation

With hydrogen bromide; mercury(II) cyanide; mercury dibromide; In acetic acid;

DOI:10.1016/0040-4039(91)80786-6

Reference yield:

alpha-L-fucose (6696-41-9) → Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester (138552-44-0)

Guidance literature:

Multi-step reaction with 7 steps

2: hydrolysis

3: Bu₂SnO

4: 60 percent / Hg(CN)2, HgBr₂

5: deacetylation under Zemplen conditions

6: benzylation

7: deallylation, acetylation

With di(n-butyl)tin oxide; mercury(II) cyanide; mercury dibromide;

DOI:10.1016/0040-4039(91)80786-6

Reference yield:

Allyl 3,4-O-isopropylidene-2-O-methyl-α-L-fucopyranoside (108182-35-0) → Acetic acid (2S,3S,4R,5R,6S)-4-benzyloxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-methoxy-6-methyl-tetrahydro-pyran-2-yl ester (138552-44-0)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrolysis

2: Bu₂SnO

3: 60 percent / Hg(CN)2, HgBr₂

4: deacetylation under Zemplen conditions

5: benzylation

6: deallylation, acetylation

With di(n-butyl)tin oxide; mercury(II) cyanide; mercury dibromide;

DOI:10.1016/0040-4039(91)80786-6

upstream raw materials:

C₃₈H₄₈O₉

1,2,3-tri-O-acetyl-4-O-methyl-α-L-rhamnopyranose

alpha-L-fucose

O²,O³-diacetyl-O⁴-methyl-α-L-rhamnopyranosyl bromide

Downstream raw materials:

C₇₆H₉₀O₁₇

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