Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester

Base Information

• Chemical Name: Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester
• CAS No.: 177595-05-0
• Molecular Formula: C₃₆H₄₉NO₁₃S
• Molecular Weight: 735.85

Synonyms:

Chemical Property of Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester

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Technology Process of Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester

There total 7 articles about Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-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: 82.0%

methanesulfonyl chloride (124-63-0) + Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4,5-dihydroxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.03,8]pentadec-11-en-9-yl ester (177595-04-9) → Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.03,8]pentadec-11-en-9-yl ester (177595-05-0)

Guidance literature:

In pyridine; for 18h; Ambient temperature;

DOI:10.1016/0040-4039(96)00495-9

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) → Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.03,8]pentadec-11-en-9-yl ester (177595-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Na₂SO₄ / CH₂Cl₂ / 1 h / Ambient temperature

2: 82 percent / pyridine / 18 h / Ambient temperature

With sodium sulfate; In pyridine; dichloromethane;

DOI:10.1016/0040-4039(96)00495-9

Reference yield:

acetic acid 7,10,13-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0(3,8)]pentadec-11-en-9-ylester (87193-98-4) → Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4-hydroxy-5-methanesulfonyloxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.03,8]pentadec-11-en-9-yl ester (177595-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / OsO₄, NMO / acetone; H₂O / 6 h / Ambient temperature

2: 1.) DMSO, oxalyl chloride, 2.) TEA / 1.) CH₂Cl₂, -60 deg C, 1 h, 2.) CH₂Cl₂, RT, 30 min

3: 78 percent / Na₂SO₄ / CH₂Cl₂ / 1 h / Ambient temperature

4: 82 percent / pyridine / 18 h / Ambient temperature

With osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; TEA; dimethyl sulfoxide; sodium sulfate; In pyridine; dichloromethane; water; acetone;

DOI:10.1016/0040-4039(96)00495-9

upstream raw materials:

methanesulfonyl chloride

Acetic acid (1R,3S,4S,5S,7S,8S,9R,10R,13S)-7,10,13-triacetoxy-4-(benzyloxyimino-methyl)-4,5-dihydroxy-8,12,15,15-tetramethyl-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester

O-benzylhydoxylamine hydrochloride

acetic acid 7,10,13-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0(3,8)]pentadec-11-en-9-ylester

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