tert-Butyl methyl ether → Ceramide NG

HRID 222837ノート

反応式

HRID 222837 の反応式
COC(C)(C)C.[C:7]([NH:26][C@H:27]([C@H:33]([OH:49])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:28](OCC)=[O:29])(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[BH4-].[Na+]>O>[C:7]([NH:26][C@H:27]([C@H:33]([OH:49])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:28][OH:29])(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

5

反応物 3

HCID 15413tert-Butyl methyl etherHCID 4311764Sodium borohydrideHCID 86638488ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

生成物 1

HCID 5283573Ceramide NG収率 95.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
23 °C

実験手順

A t-butyl methyl ether suspension (2 mL) containing ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (100 mg. 0.16 mmol) synthesized in the same method as Example 17 and sodium borohydride (20.3 mg, 0.54 mmol) was stirred at 23° C. for 48 hours. After water (5 mL) was added thereto, the reaction mixture was separated at 40° C. to separate the organic layer. It was confirmed by comparative analysis of the obtained organic layer with sample product using HPLC that the organic layer contained 86.6 mg of the title compound (yield: 93%). HPLC analysis was carried out to find that anti-form:syn-form was 93:7 and the optical purity of the anti-form was 100% ee.

後処理

  1. customthe reaction mixture was separated at 40° C.
  2. customto separate the organic layer

出典と根拠

ORDレコード
ord-40e341d1f13d45c7bb4e2e69145116c9
出典データセット
uspto-grants-2012_06
特許番号
US08207370B2

反応ノート

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