2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide

Base Information

• Chemical Name: 2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide
• CAS No.: 74844-33-0
• Molecular Formula: C₃₅H₄₂O₄P*I
• Molecular Weight: 684.594

Synonyms:2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide

Chemical Property of 2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide

Chemical Property:

Purity/Quality:

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Technology Process of 2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide

There total 3 articles about 2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide 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%

1-deoxy-1-iodo-2,3:4,5-di-O-cyclohexylidene-D-arabitol (146303-96-0) + triphenylphosphine (603-35-0) → 2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide (74844-33-0)

Guidance literature:

In sulfolane; at 110 ℃; for 24h;

DOI:10.1021/jo01310a060

Reference yield:

2,3:4,5-di-O-cyclohexylidene-D-arabitol (13266-37-0) → 2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide (74844-33-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 16 h / Ambient temperature

2: NaI, Na₂CO₃ / dimethylformamide / 1 h / 125 °C

3: 62 percent / tetrahydrothiophene 1,1-dioxide / 24 h / 110 °C

With sodium carbonate; sodium iodide; In pyridine; sulfolane; N,N-dimethyl-formamide;

DOI:10.1021/jo01310a060

Reference yield:

Toluene-4-sulfonic acid (2R,3R,2'R)-1-([2,2']bi[1,4-dioxa-spiro[4.5]decyl]-3-yl)methyl ester (32860-84-7) → 2,3:4,5-di-O-cyclohexylidene-1-deoxy-1-triphenylphosphonio-D-arabinitol iodide (74844-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaI, Na₂CO₃ / dimethylformamide / 1 h / 125 °C

2: 62 percent / tetrahydrothiophene 1,1-dioxide / 24 h / 110 °C

With sodium carbonate; sodium iodide; In sulfolane; N,N-dimethyl-formamide;

DOI:10.1021/jo01310a060

upstream raw materials:

1-deoxy-1-iodo-2,3:4,5-di-O-cyclohexylidene-D-arabitol

triphenylphosphine

2,3:4,5-di-O-cyclohexylidene-D-arabitol

Toluene-4-sulfonic acid (2R,3R,2'R)-1-([2,2']bi[1,4-dioxa-spiro[4.5]decyl]-3-yl)methyl ester

Downstream raw materials:

(2S,3R,2'R)-3-[(E)-2-((2R,3R,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-[2,2']bi[1,4-dioxa-spiro[4.5]decyl]

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(E)-(2S,3R,2'R)-2-([2,2']bi[1,4-dioxa-spiro[4.5]decyl]-3-yl)-vinyl]-6-methoxy-tetrahydro-pyran-3-ylamine

N-[(2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-((1S,2S)-2-(2R,3R,2'R)-[2,2']bi[1,4-dioxa-spiro[4.5]decyl]-3-yl-1,2-dihydroxy-ethyl)-6-methoxy-tetrahydro-pyran-3-yl]-acetamide

N-{(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(E)-(2S,3R,2'R)-2-([2,2']bi[1,4-dioxa-spiro[4.5]decyl]-3-yl)-vinyl]-6-methoxy-tetrahydro-pyran-3-yl}-acetamide

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