. Author manuscript; available in PMC: 2010 Aug 1.

Published in final edited form as: J Org Chem. 2009 Aug 21;74(16):5902–5908. doi: 10.1021/jo900844r

Table 1.

NMR data for fibrosterol sulfate A (1) (600 MHz, CD₃OD)

position	δ_C	δ_H mult (J, Hz)	HMBC	position	δ_C	δ_H mult (J, Hz)	HMBC
1α	42.8	1.14,^a m	5, 9, 10, 19	1α′	38.8	1.47, dd (14.8, 3.5)	9′, 10′, 19′
1β		2.42,^a m	2, 3, 5, 6, 19	1β′		2.06,^a m	2′, 3′, 10′, 19′
2	78.2	4.64, m	1, 3, 4, 10	2′	77.8	4.46, m	3′, 4′, 10′
3	72.1	3.58, ddd (11.8, 4.0, 4.0)	2, 4, 5	3′	68.4	4.06, m	1′, 2′, 5′
4α	27.7	2.10, m	2, 3, 5, 6, 10	4α′	26.3	2.04,^a m	2′, 3′, 5′, 6′
4β		1.62,^a m	2, 3, 5, 6, 10	4β′		1.72,^a m	5′, 6′, 10′
5	51.7	1.19,^b m	1, 3, 4, 6, 7, 9, 10	5′	44.5	1.66,^a m	1′, 3′, 4′, 6′, 7′, 9′, 10′
6	78.0	4.19,^a m	4, 5, 10	6′	78.6	4.19,^a m	4′, 5′, 10′
7α	39.8	0.98,^b m	5, 6, 8, 9, 14	7α′	39.8	1.06,^b m	6′, 8′, 14′
7β		2.36,^a m	5, 6, 8, 9, 14	7β′		2.36,^a m	5′, 6′, 8′, 9′, 14′
8	35.0	1.53,^a m	7, 9, 13, 14	8′	35.0	1.53, ^a m	7′, 9′, 13′, 14′
9	55.7	0.69,^b m	8, 10, 11, 19	9′	55.6	0.75,^b m	8′, 10′, 11′, 19′
10	37.8	——		10′	38.1	——
11α	22.1	1.55,^a m	8, 9, 12, 13	11α′	21.7	1.56,^a m	8′, 9′, 12′, 13′
11β		1.38, m	9, 10, 12	11β′		1.33,^a m	9′, 10′, 13′
12α	41.0	1.16,^b m	9, 11, 13, 18	12α′	41.3	1.18,^b m	9′, 11′, 13′, 18′
12β		2.01,^a m	9, 11, 13, 14, 18	12β′		2.02,^a m	9′, 11′, 13′, 14′, 18′
13	43.9	——		13′	43.8	——
14	56.9	1.07,^b m	8, 12, 13, 15, 18	14′	57.4	1.12,^b m	8′, 13′, 15′, 18′
15α	25.0	1.12,^a m	13, 14	15α′	25.0	1.12,^b m	13′, 14′
15β		1.56,^a m	13, 14	15β′		1.62,^a m	13′, 14′
16α	28.1	1.30,^a m	13, 15, 17	16α′	29.1	1.30,^a m	13′, 15′, 17′
16β		1.74,^a m	13, 15, 17	16β′		1.87,^a m	13′, 15′, 17′
17	54.3	1.03,^b m	13, 16, 20, 21, 22	17′	57.3	1.15,^b m	13′, 15′, 16′, 18′, 20′, 21′
18	12.4	0.71, s	12, 13, 14, 17	18′	13.1	0.72, s	12′, 13′, 14′, 17′
19	15.6	1.08, s	1, 5, 9, 10	19′	15.1	1.05, s	1′, 5′, 9′, 10′
20	43.1	1.69, m (6.6, 3.4)	13, 16, 17, 21, 22, 23	20′	37.7	1.42,^a m	16′, 17′, 22′
21	12.7	0.97, d (6.6)	17, 20, 22	21′	19.8	0.99, d (6.5)	17′, 20′, 22′
22	76.3	3.98, dd (8.7, 3.4)	17, 20, 21, 23, 24	22a′	36.9	1.69,^a m	17′, 20′, 21′, 23′, 24′
				22b′		0.99,^b m	20′, 21′, 23′, 24′
23	126.2	5.35, dd(15.7, 8.7)	20, 22, 24, 25, 27, 24′	23a′	26.6	1.42,^a m	25, 20′, 22′, 24′, 25′
				23b′		1.07,^b m	25, 22′, 24′, 25′
24	138.6	5.54, d (15.7)	22, 23, 25, 26, 27, 24′	24′	56.8	1.84,^a m
25	47.8	——		25′	157.5	——
26	24.0	1.15, s	23, 24, 25, 27, 24′	26a′	105.1	4.85^c	24′, 25′, 27′
				26b′		4.81^c	24′, 25′, 27′
27a	38.5	1.68,^a m	24, 25, 26, 24′, 25′, 27′	27′	29.8	2.43,^a m	27, 25′
27b		1.57,^a m	24, 25, 26, 24′, 25′, 27′

Signals overlapped.

Signal buried under overlapping methyl.

Overlapped with HOD signal.