Hydroxy methyl groups

Hydroxy methyl

Conformation of hydroxymethyl groups determined from ³J_H5,H6

The experimental values of the ³J_H5,H6 [1] are interpreted using two different sets of limiting values.
The values of Bock and Duus [1] are based on the Karplus equation of Haasnoot et al. [2] whereas those of Stenutz et al. [3] are based on quantum mechanical calculations in 2-hydroxymethyl tetrahydropyran (oxane).

[1] K. Bock and J.Ø. Duus, J. Carbohydr. Chem. 13 (1994) 513-543
[2] C.A.G. Haasnoot, F.A.A.M. DeLeeuw and C. Altona, Tetrahedron 36 (1980) 2783-2792.
[3] R. Stenutz, I. Carmichael, G. Widmalm and A.S. Serianni, J. Org. Chem. 67 (2002) 949-958 DOI 10.1021/jo010985i

Hydroxymethyl coupling constants and rotamer distribution in hexopyranoses
	Coupling constants			Bock & Duus			Stenutz et al.
Compound	³J_H5,H6R	³J_H5,H6S	²J_H6R,H6S	P_gt	P_gg	P_tg	P_gt	P_gg	P_tg
methyl α-D-glucopyranoside	5.49	2.39	-12.35	50	57	-7	47	42	10
methyl α-D-glucopyranoside (CD3OD)	5.64	2.40	-11.80	51	56	-7	49	41	11
methyl β-D-glucopyranoside	6.11	2.47	-12.31	56	50	-6	54	35	11
α-D-glucopyranose (DMSO)	5.00	2.30	-11.20	45	63	-8	42	48	10
β-D-glucopyranose	5.78	2.29	-12.33	53	55	-8	51	40	9
β-D-glucopyranose (DMSO)	5.90	2.20	-11.80	55	55	-10	53	39	8
methyl α-D-mannopyranoside	6.40	2.44	-12.20	59	48	-7	57	32	11
methyl 2-acetamido-2-deoxy-β-D-glucopyranoside	5.38	2.35	-12.20	49	59	-8	46	44	10
6-O-methyl-α-D-glucopyranose	5.73	2.37	-11.04	52	55	-7	50	40	10
6-O-methyl-β-D-glucopyranose	6.10	2.16	-11.20	57	53	-10	55	37	8
4,6-di-O-methyl-β-D-glucopyranose	5.64	1.96	-11.14	54	59	-13	51	43	6
methyl 6-O-acetyl-β-D-glucopyranoside	4.90	2.30	-12.30	44	64	-8	41	49	10
methyl 4,6-di-O-acetyl-β-D-glucopyranoside	3.80	2.10	-12.60	34	76	-10	30	62	8
methyl 6-O-phosphono-α-D-glucopyranoside (pH 1.3)	4.60	2.40	-11.60	41	66	-7	37	52	11
methyl 6-O-phosphonato-α-D-glucopyranoside (pH 9.3)	3.53	1.91	-12.13	32	80	-12	28	67	6
methyl 4-deoxy-α-D-xylo-hexopyranoside	6.20	3.03	-12.06	54	45	1	52	31	17
methyl 4-deoxy-β-D-xylo-hexopyranoside	7.42	3.34	-12.04	65	31	4	65	15	20
methyl 4-O-acetyl-β-D-glucopyranoside	5.90	2.20	-12.30	55	55	-10	53	39	8
methyl 4,4-di-hydroxy-α-D-xylo-hexopyranoside	8.40	2.40	-12.00	80	28	-8	79	11	10
methyl 4-thio-α-D-glucopyranoside	5.00	2.00	-12.50	47	65	-12	44	50	6
methyl 4-ammonio-4-deoxy-α-D-glucopyranoside (pH 2.0)	4.64	3.70	-12.44	34	56	10	32	43	25
methyl 4-amino-4-deoxy-α-D-glucopyranoside (pH 9.0)	5.40	2.46	-12.42	48	58	-6	46	43	11
C-propyl β-D-glucopyranoside	8.50	2.40		81	27	-8	81	10	10
methyl α-D-galactopyranoside	8.60	3.70	-11.70	75	16	9	76	0	24
methyl β-D-galactopyranoside	7.50	4.83	-11.76	58	19	24	59	5	36
β-D-galactopyranose	7.92	4.28	-11.50	65	19	16	66	4	30

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Hydroxy methyl groups

Conformation of hydroxymethyl groups determined from 3JH5,H6

Conformation of hydroxymethyl groups determined from ³J_H5,H6